Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides

Alan R Katritzky; Ilker Avan; Srinivasa R Tala

doi:10.1021/jo901612j

Efficient preparation of aminoxyacyl amides, aminoxy hybrid peptides, and alpha-aminoxy peptides

J Org Chem. 2009 Nov 20;74(22):8690-4. doi: 10.1021/jo901612j.

Authors

Alan R Katritzky¹, Ilker Avan, Srinivasa R Tala

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu

PMID: 19831362
DOI: 10.1021/jo901612j

Abstract

N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e+3e'), and (3g+3g'), aminoxy hybrid peptides 4a-h, (4a+4a'), 6a-d, 9a-e, (9a+9a'), and (9b+9b'), and alpha-aminoxy peptides 10a,b in good yields without racemization.

MeSH terms

Amides / chemical synthesis*
Amides / chemistry
Molecular Conformation
Oligopeptides / chemical synthesis*
Oligopeptides / chemistry
Stereoisomerism

Substances

Amides
Oligopeptides