DBU-Catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides

Alan R. Katritzky; Nader E. Abo-Dya; Abdelmotaal Abdelmajeid; Srinivasa R. Tala; M. S. Amine; Said A. El-Feky

doi:10.1039/c0ob00663g

DBU-Catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides

Alan R. Katritzky, Nader E. Abo-Dya, Abdelmotaal Abdelmajeid, Srinivasa R. Tala, M. S. Amine, Said A. El-Feky

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9 Scopus citations

Abstract

The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl) benzotriazoles to give larger peptides.

Original language	English (US)
Pages (from-to)	596-599
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1039/c0ob00663g
State	Published - Jan 21 2011
Externally published	Yes

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Copyright 2011 Elsevier B.V., All rights reserved.

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title = "DBU-Catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides",

abstract = "The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl) benzotriazoles to give larger peptides.",

author = "Katritzky, \{Alan R.\} and Abo-Dya, \{Nader E.\} and Abdelmotaal Abdelmajeid and Tala, \{Srinivasa R.\} and Amine, \{M. S.\} and El-Feky, \{Said A.\}",

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AU - Katritzky, Alan R.

AU - Abo-Dya, Nader E.

AU - Abdelmajeid, Abdelmotaal

AU - Tala, Srinivasa R.

AU - Amine, M. S.

AU - El-Feky, Said A.

PY - 2011/1/21

Y1 - 2011/1/21

N2 - The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl) benzotriazoles to give larger peptides.

AB - The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl) benzotriazoles to give larger peptides.

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SN - 1477-0520

VL - 9

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EP - 599

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 2

ER -

DBU-Catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides

Abstract

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