Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1...

18
Peptide Catalog 2017

Transcript of Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1...

Page 1: Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1 Fluorophore-labeled Peptide Probes 1.1.1 Alexa Fluor Series Labeled groups Absorption

PeptideCatalog 2017

Page 2: Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1 Fluorophore-labeled Peptide Probes 1.1.1 Alexa Fluor Series Labeled groups Absorption

4. PEG Modified Peptides........................................................................................................9

5. N-Methyl Modification (Me-Scan).................................................................................... 9

6. MAPs.........................................................................................................................................10

7. Peptide-Protein Conjutates..............................................................................................10

8. Stapled Peptides...................................................................................................................11

9. Cyclic Peptides......................................................................................................................11

10. Peptides’ Phosphorylation............................................................................................12

11. Peptides’ Lipidation..........................................................................................................13

12. Disulfide Formation..........................................................................................................14

13. Thioether Formation.........................................................................................................15

14. Biotinylation.........................................................................................................................15

15. Click Conjugation in Peptide Chemistry..................................................................15

1. Labeled Peptide Probes for Molecular Imaging.........................................................1

1.1 Fluorophore-Labeled Peptide Probes..............................................................................1 1.2 Radio-Labeled Peptide Probes...................................................................................... 3

2. Caspase Inhibitor; Peptidyl CMK, FMK, AOMK and CHO..................................... 4

2.1 Peptidyl CMK...............................................................................................................4

2.2 Peptidyl FMK............................................................................................................... 5

2.3 Peptidyl AOMK............................................................................................................ 5

2.4 Peptidyl Aldehyde.........................................................................................................6

3. Caspase Substrate; Peptidyl AMC, AFC and PNA...................................................7

3.1 Peptidyl AMC...............................................................................................................7

3.2 Peptidyl AFC................................................................................................................7

3.3 Peptidyl PNA................................................................................................................8

Contents

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1. Labeled Peptide Probes for Molecular Imaging

1.1 Fluorophore-labeled Peptide Probes

1.1.1 Alexa Fluor Series

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

Alexa Fluor 350

Alexa Fluor 405

Alexa Fluor 430

Alexa Fluor 488

Alexa Fluor 514

Alexa Fluor 532

Alexa Fluor 594

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

346

400

430

494

517

530

590

445

424

545

517

542

555

617

1.1.3 Cy Series

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

Cy-3

Cy-5

Cy-5.5

Cy-7

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

550

646

673

747

565

664

692

774

1.1.2 QSY Series

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

QSY-7

QSY-9

QSY-21

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

560

562

661

None

None

None

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1.1.4 Rhodamine Series

1.1.5 Fluorescein Series

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

FITC

FAM

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

494

494

518

522

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

Texas Red

RF488

TAMRA

Rhodamine B

Rhodamine Red-X

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys

N-Terminal, and Side Chain of Lys

595

498

565

555

570

615

520

580

580

590

1.1.6 Bodipy Series

Labeled groupsAbsorptionmaximum

(nm)

Emissionmaximum

(nm)Modification sites

Bodipy 493/503

Bodipy FL

Bodipy R6G

Bodipy 530/550

Bodipy TMR-X

Bodipy 558/568

Bodipy 576/589

Bodipy 581/591

Bodipy TR

Bodipy 630/650

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, and Side Chain of Lys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, and Side Chain of Lys

N-Terminal, Side Chain of Lys or Cys

N-Terminal, and Side Chain of Lys

500

505

528

534

542

558

576

584

589

625

506

513

550

554

574

569

590

592

617

640

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N N

NN

NN

OH N

N

N

NHO

O

O

OH

OOH

HO O

OHO

O

OH

O

OH

O

O

HO

O

OH

O

HO

O

OH

DOTA NOTADTPA

3

1.2 Radio-labeled Peptide Probes

N N

NN

NN

OH N

N

N

NHO

O

O

OH

OOH

HO O

OHO

O

OH

O

OH

O

O

HO

O

OH

O

HO

O

OH

DOTA NOTADTPA

N N

NN

NN

OH N

N

N

NHO

O

O

OH

OOH

HO O

OHO

O

OH

O

OH

O

O

HO

O

OH

O

HO

O

OH

DOTA NOTADTPA

1.1.7 Other Series

Labeled groups Absorptionmaximum

(nm)

Emissionmaximum

(nm)

Modification sites

Dansyl

Dabcyl

DNP

MCA

SBF

EDANS

7-OHCCA

Dacia

N-Terminal, Side Chain of Lys

N-Terminal, Side Chain of Lys

N-Terminal, and Side Chain of Lys

N-Terminal, and Side Chain of Lys

Side Chain of Cys

Side Chain of Glu or Asp

N-Terminal, and Side Chain of Lys

Side Chain of Cys

333

broad

350

358

385 and 515

335

342 (pH=4)

376

518

None

None

69

None

493

447 (pH=4)

465

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2. Caspase Inhibitor; Peptidyl CMK, FMK, AOMK and CHO

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2.1 Peptidyl CMK

Cell-permeable, irreversible inhibitor of caspase-1 (ICE). N.Rouquet et al. showed that Ac-YVAD-CMK is a potent therapeutic agent against in vivo liver apoptosis in mice.

Ac-Tyr-Val-Ala-Asp-Chloromethylketone5 mg

25 mg

$ 115

$ 459

Ac-DEVD-CMK irreversibly inhibits caspase-3. It is also active towards caspases-6, -7, -8, and -10.

Ac-Asp-Glu-Val-Asp-Chloromethylketone1 mg

5 mg

$ 31

$ 90

AAF-CMK, serine protease inhibitor. For tripeptidyl peptidase I (E.C. 3.4.14.9) a Ki value of 63 nM has been reported.

H-Ala-Ala-Phe-Chloromethylketone25 mg

100 mg

$ 186

$ 559

Biotinylated analog of the caspase-1 inhibitor YVAD-CMK, N-1330.

Biotinyl-Tyr-Val-Ala-Asp-Chloromethylketone5 mg

25 mg

$ 180

$ 716

Z-YVAD-CMK, inhibitor of caspase-1.

Z-Tyr-Val-Ala-Asp-Chloromethylketone5 mg

25 mg

$ 252

$ 1000

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2.2 Peptidyl FMK

2.3 Peptidyl AOMK

5

Methyl ester of Z-DEVD-FMK, a specific caspase-3 inhibitor. Z-D(OMe)E(OMe)VD(OMe)-FMK reduces vulnerability to the neuronal death that occurs in the aftermath of kainic acid-evoked status epilepticus (SE).

Z-Asp(OMe)-Glu(OMe)-Val-Asp(OMe)-Fluoromethylketone1 mg

5 mg

$ 152

$ 610

6-FAM-IE(OMe)TD(OMe)-FMK, the methyl ester of FAM-IETD-FMK, is a cell-permeable, non-toxic inhibitor that binds irreversibly to activated caspase-8 in apoptotic cells. The inhibitor allows to determine the amount of cells present in different stages of the apoptotic cascade and to calculate cell death kinetics. The fluorescence intensity can be measured by flow cytometry, microwell plate reader, or fluorescence microscopy.

Fluorescein-6-carbonyl-Ile-Glu(OMe)-Thr-Asp(OMe)-Fluoromethylketone0.5 mg

1 mg

$ 593

$ 1084

Cell-permeable, irreversible inhibitor of para-caspase MALT1. Z-VRPR-FMK is based on the sequence of a published optimal tetrapeptide substrate for the A. thaliana metacaspase AtMC9.

Z-Val-Arg-Pro-Arg-Fluoromethylketone0.5 mg

1 mg

$ 291

$ 542

Methyl ester of Z-VDVAD-FMK. This cell-permeable fluoromethylketone inhibits specifically caspase-2 and, to a lesser degree, caspase-3 and caspase-7.

Z-Val-Asp(OMe)-Val-Ala-Asp(OMe)-Fluoromethylketone1 mg

5 mg

$ 372

$ 1491

Biotinylated analog of the caspase-1 inhibitor Z-VAD-FMK, N-1510.

Biotinyl-Val-Ala-Asp-fluoromethylketone1 mg

5 mg

$ 711

$ 2881

Ac-YVK(biotinyl)D-AOMK, inhibitor of caspase-1 can affinity label active apoptosis-associated caspase-1 related proteases in cell-free extracts. The substrate preferences of these labeled proteases can be analyzed using cleavage site peptides.

Ac-Tyr-Val-Lys(biotinyl)-Asp-2,6-Dimethylbenzoyloxymethylketone1 mg

5 mg

$ 57

$ 230

Ac-YVAD-AOMK is a highly selective, competitive and irreversible inhibitor of caspase-1 (ICE). Ac-YVAD-AOM inactivates the enzyme with a rate limited by diffusion and is relatively inert toward other bionucleophiles such as glutathione, making it an excellent candidate for in vivo studies of enzyme inhibitors.

Ac-Tyr-Val-Ala-Asp-2,6-dimethylbenzoyloxymethylketone5 mg

25 mg

$ 143

$ 576

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2.4 Peptidyl Aldehyde

6

The peptide aldehyde Ac-IETD-CHO corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 172-175). In a concentration range of 0.5 µM, Ac-IETD-CHOblocked the formation of the p17 subunit and concomitantly induced the accumulation of the 32 kD precursor.

Ac-Ile-Glu-Thr-Asp-Aldehyde5 mg

25 mg

$ 143

$ 576

Ac-YVAD-CHO is a potent, specific, reversible inhibitor of caspase-1 (ICE). It displayed a Ki of 0.2 ± 0.1 nM for recombinant human caspase-1.

Ac-Tyr-Val-Ala-Asp-Aldehyde5 mg

25 mg

$ 143

$ 576

The peptide aldehyde Ac-ESMD-CHO corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 25-28). In a concentration range of 2.5 - 5 µM, it blocked the formation of the p17 subunit and concomitantly induced the accumulation of the p20 peptide.

Ac-Glu-Ser-Met-Asp-Aldehyde5 mg

25 mg

$ 143

$ 576

Ac-LEVD-CHO, inhibitor of caspase-4 (ICH-2).

Ac-Leu-Glu-Val-Asp-Aldehyde5 mg

25 mg

$ 143

$ 576

This biotinylated apopain inhibitor has successfully been used for the affinity purification - on a streptavidin-agarose column - of caspase-3 (apopain), the enzyme that cleaves the poly(ADP-ribose) polymerase (PARP). Biotinyl-DE-VD-CHO showed an inhibitory activity comparable to that of the N-acetylated analog inhibitor (H-2496) (IC50 = 0.2 nM).

Biotinyl-Asp-Glu-Val-Asp-Aldehyde5 mg

25 mg

$ 180

$ 711

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3. Caspase Substrate; Peptidyl AMC, AFC and PNA

3.1 Peptidyl AMC

3.2 Peptidyl AFC

Z-LLE-AMC is an excellent fluorogenic substrate for measuring the peptidylglutamyl-peptide-hydrolyzing (PGPH) activity of the 20S proteasome. See also e.g. I-1085 (for assaying the trypsin-like activity) and I-1395 (for determining the chymotrypsin-like activity).

Z-Leu-Leu-Glu-AMC5 mg

25 mg

$ 172

$ 689

Acetyl-KQKLR-AMC, fluorogenic substrate for cathepsin S.

Ac-Lys-Gln-Lys-Leu-Arg-AMC1 mg

5 mg

$ 115

$ 466

Acetyl-KQKLR-AMC, fluorogenic substrate for cathepsin S.

Ac-Phe-Arg-AMC50 mg

250 mg

$ 244

$ 976

Suc-AAV-AMC is cleaved by neprilysin 2.

Suc-Ala-Ala-Val-AMC50 mg

250 mg

$ 477

$ 1922

Z-RLRGG-AMC is a fluorogenic substrate for the deubiquitinating enzyme isopeptidase T (IPaseT) and other ubiqui-tin C-terminal hydrolases (UCHs) based on the C-termini of ubiquitin with a kcat/Km value of 95 M-¹s-¹. Together with our product I-1685 it is used in continuous assays for precise mechanistic studies or microtiter plate assays for high-throughput inhibitor screening.

Z-Arg-Leu-Arg-Gly-Gly-AMC25 mg

100 mg

$ 143

$ 430

The fluorogenic substrate Z-IETD-AFC corresponds to one of the cleavage sites of the inactive 32 kD caspase-3 precursor (amino acids 172-175). Substrate for granzyme B.

Z-Ile-Glu-Thr-Asp-AFC5 mg

25 mg

$ 265

$ 1062

The presence of halogen substituents at the fluorescent group improves membrane permeability of the YVAD-de-rived caspase-1 substrate.

Ac-Tyr-Val-Ala-Asp-AFC5 mg

25 mg

$ 172

$ 689

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3.3 Peptidyl PNA

8

Z-VEID-AFC, fluorogenic substrate for caspase-6 (Mch2).

Z-Val-Glu-Ile-Asp-AFC ammonium salt5 mg

25 mg

$ 240

$ 961

Ac-WEHD-AFC, fluorogenic caspase-1 substrate

Ac-Trp-Glu-His-Asp-AFC trifluoroacetate salt10 mg

50 mg

$ 245

$ 867

Z-VEID-AFC, fluorogenic substrate for caspase-6 (Mch2).

Z-Val-Glu-Ile-Asp-AFC5 mg

25 mg

$ 240

$ 961

Ac-AAPF-pNA, chromogenic substrate for chymotrypsin and an excellent substrate for proteinase yscD (saccharoly-sin).

Ac-Ala-Ala-Pro-Phe-PNA50 mg

250 mg

$ 338

$ 1288

The cleavage of the chromogenic caspase-3 substrate Ac-DEVD-pNA can be monitored at 405 nm.

Ac-Asp-Glu-Val-Asp-PNA5 mg

25 mg

$ 72

$ 286

Boc-QAR-pNA, chromogenic substrate for trypsin and matriptase-2.

Boc-Gln-Ala-Arg-PNA50 mg

250 mg

$ 178

$ 717

Suc-AAF-pNA, a sensitive substrate for subtilisins, proteinase K, thermitase, and chymotrypsin.

Suc-Ala-Ala-Phe-PNA250 mg

1000 mg

$501

$1506

Astacin, a zinc-endopeptidase from the crayfish Astacusastacus, hydrolyzes the pentaalanine substrate Suc-AAAAA-pNA at two positions. The first, highly specific cleavage yields Suc-Ala-Ala and Ala-Ala-Ala-pNA (L-1090); the second, much less specific cleavage releases p-nitroaniline from the generated chromogenic substrate.

Suc-Ala-Ala-Ala-Ala-Ala-PNA25 mg

100 mg

$406

$1186

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4. PEG Modified Peptides

H-Pro-PEG4-Cys-Pro-Glu-Thr-Asp-Asp-Arg-Pro-Cys-OH(Cys&Cys disulfide)

10 mg

50 mg

$ 254

$ 1016

PEG2000-Gly-Pro-Gly-Thr-Asp-Thr-Lys-Ala-Tyr-Val-Arg-Asp-Ser-Tyr-Thr-Ala-Leu-Ser-Ser-Ala-Leu-Arg-Pro-Asp-Ile-Val-Gln-Arg-Arg-Phe-Ala-Gly-Ser-Thr-Arg-His-His-Leu-Arg-Lys-Lys-OH

5 mg

25 mg

$ 1016

$ 4237

5. N-Methyl Modification (Me-Scan)

c(RGDf(NMe)V) peptide Cilengitide (EMD 121974; NSC 707544) is a potent integrin inhibitor for αvβ3 and αvβ5 integ-rin with IC50 of 4.1 nM and 79 nM, respectively; ~10-fold selectivity against gpIIbIIIa.

Cyclo(Arg-Gly-Asp-D-Phe-NMe-Val)100 mg

1000 mg

$ 508

$ 1525

Thispeptide is the fragment of Histone H3 (15-39) monomethylated at Lys27 with a C-terminal followed by a biotinylat-ed Lys.

Ala-Pro-Arg-Lys-Gln-Leu-Ala-Thr-Lys-Ala-Ala-Arg-Lys(Me)-Ser-Ala-Pro-Ala-Thr-Gly-Gly-Val-Lys-Lys-Pro-His-Lys(Biotin)-NH2

1 mg

5 mg

$ 180

$ 423

TSRHK-K(Me)-LMFKT peptide is derived from amino acid residues 377-387 of human p53 tumor suppressor protein, with monomethylation at Lys382. Methylation of p53 at Lys382 inhibits expression of p53 target genes and decreases apoptotic and cell cycle arrest functions of p53. This allows p53-dependent DNA repair without apoptosis. Levels of this peptide decrease in response to DNA damage

Thr-Ser-Arg-His-Lys-Lys(Me)-Leu-Met-Phe-Lys-Thr1 mg

5 mg

$ 180

$ 423

Efficient fluorogenic substrate for two matrix metalloproteinases: interstitial collagenase (MMP-1) and gelatinase (MMP-9). Dnp-Pro-Cha-Gly-Cys(Me)-His-Ala-Lys(N-Me-Abz)-amide has favorable solubility characteristics. Both enzymes cleave this substrate between Gly and Cys(Me) (Smc), liberating a cleavage product with a fluorescence signal suitable for inhibitor screening and determining Ki values. The major advantage of this FRET substrate is its adaptability to filters commonly available on commercial plate readers (excitation at 365 nm and emission at 450 nm).

Dnp-Pro-β-cyclohexyl-Ala-Gly-Cys(Me)-His-Ala-Lys(NMe-Abz)-NH25 mg

25 mg

$ 423

$ 813

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7. Peptide-Protein Conjutates

This linear AVP analog is an extremely high-affinity and selective antagonist at V-1a vasopressin receptors. Conve-nient derivatization of the Lysε-amino group with AMC or biotin leads to highly selective V-1a ligands that are, e.g., useful for receptor localization and purification studies.

Phenylac-D-Tyr(Me)-Phe-Gln-Asn-Arg-Pro-Arg-Lys-NH25 mg

25 mg

$ 254

$ 372

6. MAPs

(RGFAFVTF)8-MAP, multiple antigenic peptide.

(H-Arg-Gly-Phe-Ala-Phe-Val-Thr-Phe)8-MAP1 mg

5 mg

$ 644

$ 2542

Multiple antigenic peptide (KILNDLSSDAPGVPR)8-MAP, the sequence corresponds to rat CREB (136-150).

(H-Lys-Ile-Leu-Asn-Asp-Leu-Ser-Ser-Asp-Ala-Pro-Gly-Val-Pro-Arg)8-MAP1 mg

5 mg

$ 677

$ 2542

(KGLGLKGGLG)4-MAP, multiple antigenic peptide.

(H-Lys-Gly-Leu-Gly-Leu-Lys-Gly-Gly-Leu-Gly)4-MAP25 mg

100 mg

$135

$423

1)KLH (Keyhole Limpet Hemocyanin) 2)BSA (Bovine Serum Albumin) 3)OVA (Ovalbumin)

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8. Stapled Peptides

9. Cyclic Peptides

An RGD tumor-targeting peptide, which binds to αvβ3 receptors. It can be easily conjugated to fluorophore tags, chelators, or carriers. Palecek et al. converted the ε-amino group into the azide by diazo transfer allowing further functionalization by click chemistry. Mercapto groups can be introduced via acylation of this peptide with S-acetylthio-acetic acid (SATA).

Cyclo(Arg-Gly-Asp-D-Phe-Lys)5 mg

25 mg

$ 254

$ 508

Melanotan II, a cyclic MSH analog, is a potent full agonist of the melanocortin-3 and melanocortin-4 receptors (MC3-R and MC4-R). Intracerebroventricular administration of MTII inhibited feeding in four different mouse models of hyper-phagia. MTII is a valuable tool for the study of the agouti obesity syndrome and of the role of melanocortinergic neurons in feeding.

Ac-Nle-cyclo(-Asp-His-D-Phe-Arg-Trp-Lys)5 mg

25 mg

$ 254

$ 1016

It has been demonstrated that the RGD-containing peptide, c(GRGDSPA), inhibited the binding of fibronectin to stimulated platelets with IC50=0.223 µM. c(GRGDSPA) also blocked thrombin-induced platelet aggregation with IC50= 32 µM, but was less potent than native fibronectin in this respect.

Cyclo(Gly-Arg-Gly-Asp-Ser-Pro-Ala)5 mg

25 mg

$ 508

$ 847

This sulfur-bridged cyclopeptide is a potent inhibitor of the binding of glycoprotein IIb/IIIa to fibrinogen with an IC50 of 1.5 nM. Furthermore, it is a highly potent inhibitor of fibrinogen-mediated platelet aggregation (IC50= 0.15 µM). Its antithrombotic activity in vivo may render this compound useful in the treatment of arterial thromboembolic diseases.

Cyclo(-D-Tyr-Arg-Gly-Asp-Cys(carboxymethyl)-OH) sulfoxide1 mg

5 mg

$ 161

$ 644

Somatostatin antagonist.

Cyclo(7-aminoheptanoyl-Phe-D-Trp-Lys-Thr(Bzl))5 mg

25 mg

$ 355

$ 1389

FITC-betaAla-Glu-Ile-Trp-Leu-Ala-Gln-Glu-Leu-Arg-S5-Ile-Gly-Asp-R8-Phe-Asn-Ala-Tyr-Tyr-Ala Stapled between S5 &R8)

1 mg

5 mg

$ 644

$ 2542

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10. Peptides’ Phosphorylation

WFYpSPR-pNA, chromogenic substrate for Pin1, an essential and conserved mitotic peptidyl-prolyl isomerase (PPIase), that specifically recognizes the phosphoserine-proline bonds present in mitotic phosphoproteins.

H-Trp-Phe-Tyr-Ser(PO3H2)-Pro-Arg-pNA1 mg

5 mg

$ 135

$ 542

A protein tyrosine phosphatases substrate. The use of this phosphopeptide substrate is highly recommended for the detection and characterization of a wide variety of intracellular and receptor-linked protein tyrosine phosphatases, particularly when limiting amounts of tissue extracts or immunoprecipitates are concerned.

H-Glu-Asn-Asp-Tyr(PO3H2)-Ile-Asn-Ala-Ser-Leu-OH1 mg

5 mg

$ 250

$ 1000

The phosphopeptide EPQ(p)YEEIPIYL is derived from the hamster polyoma middle-T antigen. It binds with high affinity and specificity to the Src homology-2 (SH2) domains of the protein tyrosine kinases p56 lck and p60 src. The side chains of residues pY (phosphotyrosine) and Ile at position pY+3 were shown to occupy deep binding pockets of either SH2 domain surface.

H-Glu-Pro-Gln-Tyr(PO3H2)-Glu-Glu-Ile-Pro-Ile-Tyr-Leu-OH1 mg

5 mg

$ 254

$ 1016

The small mammalian heat shock proteins show a highly conserved amino acid sequence and are suggested to play a major role in the increased thermal resistance acquired by cells after exposure to heat shock. They possess two major sites of phosphorylation which are each located in the conserved protein kinase phosphorylation site motif Arg-X-X-Ser. The above-mentioned phosphopeptide, which contains the second site of phosphorylation, has been isolated from a tryptic digest of phosphorylated native and recombinant mouse hsp 25. Only Ser86, the first of the three serine residues, is phosphorylated

H-Cys-Leu-Asn-Arg-Gln-Leu-Ser(PO3H2)-Ser-Gly-Val-Ser-Glu-Ile-Arg-OH1 mg

5 mg

$ 305

$ 1220

This peptide corresponds to residues 317 to 320 of the oncogenic protein Shc. Similar phosphotyrosine motifs are also found in receptor tyrosine kinases and substrates of them. This peptide binds with high affinity (18 nM) to the SH2 domain of the growth factor bound-2 protein (Grb2). It is a useful inhibitor of the interaction of Grb2 with Shc, or with other Grb-2-binding proteins involved in the cell signaling cascade.

H-Tyr(PO3H2)-Val-Asn-Val-OH1 mg

5 mg

$ 237

$ 949

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11. Peptides’ Lipidation

13

The non-toxic lipopeptide Pam3CSKKKK is a highly effective adjuvant for parenteral, oral and nasal immunizations. It readily dissolves in aqueous solvents and might also be applicable for DNA immunizations.

Palmitoyl-Cys((RS)-2, 3-di(palmitoyloxy)-propyl)-Ser-Lys-Lys-Lys-Lys-OH5 mg

25 mg

$ 762

$ 3050

The synthetic lipopeptide analog Pam3Cys-Ala-Gly, which corresponds to the N-terminal region of a bacterial lipopro-tein, is a potent activator of macrophages. It is suggested that the uptake of Pam3CAG into macrophages involves the aggregation of membrane proteins.

Palmitoyl-Cys((RS)-2, 3-di(palmitoyloxy)-propyl)-Ala-Gly-OH5 mg

25 mg

$ 254

$ 1016

The myristylated pentapeptide Myr-KRTLR is an effective inhibitor of the protein kinase C (PKC)-catalyzed histone phosphorylation (inhibitory constant, IC50 = 75 µM). It competes with the phosphoacceptor substrate of PKC and interacts with the phospholipid cofactor of the enzyme.

Myristoyl-Lys-Arg-Thr-Leu-Arg-OH5 mg

25 mg

$ 69

$ 271

The myristoylated nonapeptide Myr-FARKGALRQ corresponding to the pseudosubstrate domain of PKC-α and -β subtypes represents a selective and cell-permeable inhibitor of PKC in intact cells.

Myristoyl-Phe-Ala-Arg-Lys-Gly-Ala-Leu-Arg-Gln-OH5 mg

25 mg

$ 228

$ 847

Ghrelin, a peptide hormone produced by the stomach oxyntic cells plays a crucial role in appetite regulation. It binds to the growth hormone secretagogue receptor (GHS-R), which stimulates the release of GH. Ghrelin, which promotes food uptake and body weight increase, acts as an antagonist of leptin. Thus, it has become an important tool in obesi-ty research.Additionally, ghrelin is involved in the bone metabolism, in reproduction, and in the immune system.

H-Gly-Ser-Ser(octanoyl)-Phe-Leu-Ser-Pro-Glu-His-Gln-Lys-Ala-Gln-Gln-Arg-Lys-Glu-Ser-Lys-Lys-Pro-Pro-Ala-Lys-Leu-Gln-Pro-Arg-OH

1 mg

5 mg

$ 491

$ 2033

Page 16: Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1 Fluorophore-labeled Peptide Probes 1.1.1 Alexa Fluor Series Labeled groups Absorption

12. Disulfide Formation

14

Potent vasoconstrictor that acts on endothelia cells and on the underlying smooth muscle cells as a modulator of vascular tone. ET-1 displays selectivity for ETA receptor.

Cys-Ser-Cys-Ser-Ser-Leu-Met-Asp-Lys-Glu-Cys-Val-Tyr-Phe-Cys-His-Leu-Asp-Ile-Ile-Trp(Cys1&Cys15 Bridge, Cys3&Cys11 Bridge)(Endothelin-1)

1 mg

5 mg

$ 203

$ 847

This peptide displays a higher contractor activity on mouse and guinea pig, whereas it is weaker in its vasoconstric-tor activity.

Cys-Ser-Cys-Asn-Ser-Trp-Leu-Asp-Lys-Glu-Cys-Val-Tyr-Phe-Cys-His-Leu-Asp-Ile-Ile-Trp(Cys1&Cys15Bridge, Cys3&Cys11Bridge)(VasiactuveIntest-inalContractor)

1 mg

5 mg

$ 203

$ 847

Relaxin H2 is the major stored and circulating isoform of the peptide hormone relaxin in humans. This pregnancy hormone has also shown cardioprotective activity. The observed long-term effects of relaxin H2 on connective tissues may be due to alterations in the turnover of collagen and proteoglycans.

(Pyr-Leu-Tyr-Ser-Ala-Leu-Ala-Asn-Lys-Cys-Cys-His-Val-Gly-Cys-Thr-Lys-Arg-Ser-Leu-Ala-Arg-Phe-Cys-OH)A(H-Asp-Ser-Trp-Met-Glu-Glu-Val-Ile-Lys-Leu-Cys-Gly-Arg-Glu-Leu-Val-Arg-Ala-Gln-Ile-Ala-Ile-Cys-Gly-Met-Ser-Thr-Trp-Ser-OH)B (Cys10A&Cys15A Bridge, Cys11A&Cys11B Bridge, Cys24A &Cys23B Bridge) (Relaxin H2 Human)

1 mg

5 mg

$ 1355

$ 5423

Relaxin H2 is the major stored and circulating isoform of the peptide hormone relaxin in humans. This pregnancy hormone has also shown cardioprotective activity. The observed long-term effects of relaxin H2 on connective tissues may be due to alterations in the turnover of collagen and proteoglycans.

(H-Asp-Val-Leu-Ala-Gly-Leu-Ser-Ser-Ser-Cys-Cys-Lys-Trp-Gly-Cys-Ser-Lys-Ser-Glu-Ile-Ser-Ser-Leu-Cys-OH)A(H-Arg-Ala-Ala-Pro-Tyr-Gly-Val-Arg-Leu-Cys-Gly-Arg-Glu-Phe-Ile-Arg-Ala-Val-Ile-Phe-Thr-Cys-Gly-Gly-Ser-Arg-Trp-OH)B (Cys10&Cys15 Bridge A, Cys11A&Cys10B Bridge, Cys24A &Cys22B Bridge) (Relaxin H3 Human)

1 mg

5 mg

$ 1355

$ 5423

This peptide acts as substrate for the disulfide bond-forming enzymes protein disulfide-isomerase (PDI) and DsbA (a periplasmic protein thiol:disulfide oxidoreductase). NRCSQGSCWN permits the rapid determination of the pH-depen-dence of the activity of both enzymes.

H-Asn-Arg-Cys-Ser-Gln-Gly-Ser-Cys-Trp-Asn-OH (Disulfide bond)5 mg

25 mg

$ 254

$ 847

Page 17: Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1 Fluorophore-labeled Peptide Probes 1.1.1 Alexa Fluor Series Labeled groups Absorption

13. Thioether Formation

14. Biotinylation

15. Click Conjugation in Peptide Chemistry

15

(Biotinyl-ACTH (1-39) (human))

Biotinyl-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-Gly-Lys-Lys-Arg-Arg-Pro-Val-Lys-Val-Tyr-Pro-Asn-Gly-Ala-Glu-Asp-Glu-Ser-Ala-Glu-Ala-Phe-Pro-Leu-Glu-Phe-OH

1 mg

5 mg

$ 128

$ 508

(Biotinyl-pTH (1-34) (human)

Biotinyl-Ser-Val-Ser-Glu-Ile-Gln-Leu-Met-His-Asn-Leu-Gly-Lys-His-Leu-Asn-Ser-Met-Glu-Arg-Val-Glu-Trp-Leu-Arg-Lys-Lys-Leu-Gln-Asp-Val-His-Asn-Phe-OH trifluoroacetate salt

5 mg

25 mg

$ 203

$ 593

GLP-1 (7-36)-Lys(biotinyl) amide (human, bovine, guinea pig, mouse, rat)

H-His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Lys-Glu-Phe-Ile-Ala-Trp-Leu-Val-Lys-Gly-Arg-Lys(biotinyl)-NH2

1 mg

5 mg

$ 423

$ 1694

This biotinylated ω-conotoxin GVIA is a useful ligand for the characterization of calcium channels

Biotinyl-εAhx-Cys-Lys-Ser-Hyp-Gly-Ser-Ser-Cys-Ser-Hyp-Thr-Ser-Tyr-Asn-Cys-Cys-Arg-Ser-Cys-Asn-Hyp-Tyr-Thr-Lys-Arg-Cys-Tyr-NH2(Cys2 & Cys17 Bridge, Cys9 & Cys20, Cys16 & Cys27 Bridge)

1 mg

5 mg

$ 430

$ 1694

Biotinyl-α-CGRP (human) trifluoroacetate salt

Biotinyl-Ala-Cys-Asp-Thr-Ala-Thr-Cys-Val-Thr-His-Arg-Leu-Ala-Gly-Leu-Leu-Ser-Arg-Ser-Gly-Gly-Val-Val-Lys-Asn-Asn-Phe-Val-Pro-Thr-Asn-Val-Gly-Ser-Lys-Ala-Phe-NH2 trifluoroacetate salt (Disulfide bond)

1 mg

5 mg

$ 1322

$ 5084

Cyclo(C4-Tyr-Leu-Asp-Gly-Cys-Pro-Ile-Ala) (C4&Cys Side Chain ThioesterBridge)

5 mg

20 mg

$ 338

$ 1694

Ala-Tyr-Ile-Gln-Asn-HomoCys-Pro-Lys-Gly-NH2

(Ala&HomoCys Side Chain ThioesterBridge)5 mg

20 mg

$ 5000

$ 3389

Page 18: Peptide Catalog 2017 · 2017. 11. 10. · 1 1. Labeled Peptide Probes for Molecular Imaging 1.1 Fluorophore-labeled Peptide Probes 1.1.1 Alexa Fluor Series Labeled groups Absorption

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