Syntheses of hydrazino peptides and conjugates

Siva S. Panda; Claudia El-Nachef; Kiran Bajaj; Alan R. Katritzky

doi:10.1002/ejoc.201201731

Syntheses of hydrazino peptides and conjugates

Siva S. Panda, Claudia El-Nachef, Kiran Bajaj, Alan R. Katritzky

Chemistry and Physics

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17 Scopus citations

Abstract

(α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42-71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49-88 %. Benzyloxycarbonyl-protected hybrid hydrazino dipeptides and benzyloxycarbonyl-protected hydrazino aminoacyl conjugates with N-, S-, O-, and C-nucleophiles were prepared by using benzotriazole methodology.

Original language	English (US)
Pages (from-to)	4156-4162
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	19
DOIs	https://doi.org/10.1002/ejoc.201201731
State	Published - Jul 2013

Keywords

Acylation
Conjugates
Microwave chemistry
Peptides
Synthetic methods

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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10.1002/ejoc.201201731

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title = "Syntheses of hydrazino peptides and conjugates",

abstract = "(α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42-71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49-88 %. Benzyloxycarbonyl-protected hybrid hydrazino dipeptides and benzyloxycarbonyl-protected hydrazino aminoacyl conjugates with N-, S-, O-, and C-nucleophiles were prepared by using benzotriazole methodology.",

keywords = "Acylation, Conjugates, Microwave chemistry, Peptides, Synthetic methods",

author = "Panda, {Siva S.} and Claudia El-Nachef and Kiran Bajaj and Katritzky, {Alan R.}",

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T1 - Syntheses of hydrazino peptides and conjugates

AU - Panda, Siva S.

AU - El-Nachef, Claudia

AU - Bajaj, Kiran

AU - Katritzky, Alan R.

PY - 2013/7

Y1 - 2013/7

N2 - (α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42-71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49-88 %. Benzyloxycarbonyl-protected hybrid hydrazino dipeptides and benzyloxycarbonyl-protected hydrazino aminoacyl conjugates with N-, S-, O-, and C-nucleophiles were prepared by using benzotriazole methodology.

AB - (α-Benzyloxycarbonyl-aminoacyl)benzotriazolides (Cbz = benzyloxycarbonyl) underwent a coupling reaction with α-hydrazino acids under microwave irradiation to form hybrid hydrazino dipeptides (42-71 %). Chiral acylations of β-N-Cbz-α-hydrazino acylbenzotriazolides were successfully carried out with N-, S-, O-, and C-nucleophiles in yields of 49-88 %. Benzyloxycarbonyl-protected hybrid hydrazino dipeptides and benzyloxycarbonyl-protected hydrazino aminoacyl conjugates with N-, S-, O-, and C-nucleophiles were prepared by using benzotriazole methodology.

KW - Acylation

KW - Conjugates

KW - Microwave chemistry

KW - Peptides

KW - Synthetic methods

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DO - 10.1002/ejoc.201201731

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JF - Justus Liebigs Annalen der Chemie

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Syntheses of hydrazino peptides and conjugates

Abstract

Keywords

ASJC Scopus subject areas

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