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 *alison.thompson@dal.ca; (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

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

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

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

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

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

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 9c

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 10a

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 10b

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 10c

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 2a

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

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

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

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 3b

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 3c

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 4a

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

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 18b

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 18c

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 19b

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 19c

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 24a

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 24b

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 24c

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 25a

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 25b

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 25c

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 26a

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 26b

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 26c

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 27a

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 27b

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 27c

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 28a

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 28b

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 28c

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 29a

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 29b