Figliola, Marchal, Step-wise synthetic approach key to Groves and … · 2019-04-23 · Figliola,...
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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Supplemental Information
Step-wise synthetic approach is necessary to access g-conjugates of folate: folate-conjugated prodigiosenes
Carlotta Figliola,^ Estelle Marchal,^ Brandon R. Groves and Alison Thompson*
Department of Chemistry, Dalhousie University, PO BOX 15000, Halifax, NS, B3H 4R2, Canada
^Equal contributions *[email protected]; (T) 1-902-494-3305
Table of Contents 1H and 13C NMR Spectra ...........................................................................................................................2
1H and 13C NMR in CDCl3 of 8a ...........................................................................................................................21H and 13C NMR in CD3OD of 8b .........................................................................................................................31H and 13C NMR in CDCl3 of 8c ............................................................................................................................41H and 13C NMR in CDCl3 of 9a ............................................................................................................................51H and 13C NMR in CDCl3 of 9b ...........................................................................................................................61H and 13C NMR in CDCl3 of 9c ............................................................................................................................71H and 13C NMR in CDCl3 of 10a ..........................................................................................................................81H and 13C NMR in CDCl3 of 10b .........................................................................................................................91H and 13C NMR in CDCl3 of 10c ........................................................................................................................101H and 13C NMR in DMSO-d6 of 2a ....................................................................................................................111H and 13C NMR in CD3OD of 2b .......................................................................................................................121H and 13C NMR in DMSO-d6 of 2c ....................................................................................................................131H and 13C NMR in CDCl3 of 3a ..........................................................................................................................141H and 13C NMR in CDCl3 of 3b .........................................................................................................................151H and 13C NMR in CDCl3 of 3c ..........................................................................................................................161H and 13C NMR in CDCl3 of 4a ..........................................................................................................................171H NMR in DMSO-d6 of 11 .................................................................................................................................181H and 13C NMR in CDCl3 of 18b .......................................................................................................................191H and 13C NMR in CDCl3 of 18c .......................................................................................................................201H and 13C NMR in CDCl3 of 19b .......................................................................................................................211H and 13C NMR in CDCl3 of 19c .......................................................................................................................221H and 13C NMR in DMSO-d6 of 24a ..................................................................................................................231H and 13C NMR in DMSO-d6 of 24b .................................................................................................................241H and 13C NMR in CDCl3 of 24c ........................................................................................................................251H and 13C NMR in CDCl3 of 25a ........................................................................................................................261H and 13C NMR in CDCl3 of 25b .......................................................................................................................271H and 13C NMR in CDCl3 of 25c ........................................................................................................................281H and 13C NMR in CDCl3 of 26a ........................................................................................................................291H and 13C NMR in CDCl3 of 26b .......................................................................................................................301H and 13C NMR in CDCl3 of 26c ........................................................................................................................311H and 13C NMR in DMSO-d6 of 27a ..................................................................................................................321H and 13C NMR in DMSO-d6 of 27b .................................................................................................................331H and 13C NMR in DMSO-d6 of 27c ..................................................................................................................341H and 13C NMR in DMSO-d6 of 28a ..................................................................................................................351H and 13C NMR in DMSO-d6 of 28b ..................................................................................................................361H and 13C NMR in DMSO-d6 of 28c ..................................................................................................................371H and 13C NMR in DMSO-d6 of 29a ..................................................................................................................381H and 13C NMR in DMSO-d6 of 29b ..................................................................................................................39
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2019
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR Spectra 1H and 13C NMR in CDCl3 of 8a
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CD3OD of 8b
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CDCl3 of 8c
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CDCl3 of 9a
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CDCl3 of 9b
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1H and 13C NMR in CDCl3 of 9c
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1H and 13C NMR in CDCl3 of 10a
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1H and 13C NMR in CDCl3 of 10b
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1H and 13C NMR in CDCl3 of 10c
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1H and 13C NMR in DMSO-d6 of 2a
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CD3OD of 2b
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in DMSO-d6 of 2c
N
O
HN
O
HN
O
HN 8
NH2
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H and 13C NMR in CDCl3 of 3a
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1H and 13C NMR in CDCl3 of 3b
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1H and 13C NMR in CDCl3 of 3c
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1H and 13C NMR in CDCl3 of 4a
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Figliola, Marchal, Step-wise synthetic approach key to g-conjugates of folate: Groves and Thompson folate-conjugated prodigiosenes
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1H NMR in DMSO-d6 of 11
1H NMR in DMSO-d6 of octylamine-FA conjugate
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1H and 13C NMR in CDCl3 of 18b
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1H and 13C NMR in CDCl3 of 18c
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1H and 13C NMR in CDCl3 of 19b
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1H and 13C NMR in CDCl3 of 19c
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1H and 13C NMR in DMSO-d6 of 24a
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1H and 13C NMR in DMSO-d6 of 24b
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1H and 13C NMR in CDCl3 of 24c
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1H and 13C NMR in CDCl3 of 25a
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1H and 13C NMR in CDCl3 of 25b
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1H and 13C NMR in CDCl3 of 25c
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1H and 13C NMR in CDCl3 of 26a
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1H and 13C NMR in CDCl3 of 26b
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1H and 13C NMR in CDCl3 of 26c
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1H and 13C NMR in DMSO-d6 of 27a
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1H and 13C NMR in DMSO-d6 of 27b
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1H and 13C NMR in DMSO-d6 of 27c
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1H and 13C NMR in DMSO-d6 of 28a
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1H and 13C NMR in DMSO-d6 of 28b
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1H and 13C NMR in DMSO-d6 of 28c
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1H and 13C NMR in DMSO-d6 of 29a
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1H and 13C NMR in DMSO-d6 of 29b