A Tamao–Fleming oxidation route to dipeptides bearing N,O-acetal functionality

Sherif M.S Ibrahim; Koushik Banerjee; Kara A Slater; Gregory K Friestad

doi:10.1016/j.tetlet.2017.11.036

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A Tamao–Fleming oxidation route to dipeptides bearing N,O-acetal functionality

Journal article

Open access

Peer reviewed

A Tamao–Fleming oxidation route to dipeptides bearing N,O-acetal functionality

Sherif M.S Ibrahim, Koushik Banerjee, Kara A Slater and Gregory K Friestad

Tetrahedron letters, Vol.58(52), pp.4864-4866

12/27/2017

DOI: 10.1016/j.tetlet.2017.11.036

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Abstract

[Display omitted] •Tamao–Fleming oxidation conditions to prepare N,O-acetals.•Preparation of N,O-acetals linked to the peptide bond nitrogen.•Traceless linker for potential application to bioconjugates and prodrugs. Tamao–Fleming oxidation of the N-dimethylphenylsilylmethyl group linked to the nitrogen of a peptide bond enables access to dipeptide N,O-acetal functionality. The N-silylmethyl functionality serves as a latent form of the N,O-acetal which is revealed after peptide bond construction.

Bioconjugate chemistry

N,O-Acetals

Oxidation reactions

Peptides

Prodrugs

Details

Title: Subtitle: A Tamao–Fleming oxidation route to dipeptides bearing N,O-acetal functionality
Creators: Sherif M.S Ibrahim
Koushik Banerjee
Kara A Slater
Gregory K Friestad
Resource Type: Journal article
Publication Details: Tetrahedron letters, Vol.58(52), pp.4864-4866
Publisher: Elsevier Ltd
DOI: 10.1016/j.tetlet.2017.11.036
ISSN: 0040-4039
eISSN: 1873-3581
Grant note: DOI: 10.13039/100000001, name: National Science Foundation, award: CHE-1362111
Language: English
Date published: 12/27/2017
Academic Unit: Chemistry
Record Identifier: 9984216560802771

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