Access to Enantiopure α‑Hydrazino Acids for N‑Amino Peptide Synthesis

Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydra...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 3; pp. 1833 - 1841
Main Authors Kang, Chang Won, Sarnowski, Matthew P, Elbatrawi, Yassin M, Del Valle, Juan R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.02.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
METHYLATION
OXAZIRIDINES
SOLID-PHASE SYNTHESIS
PEPTOIDS
LIBRARY
CHEMISTRY
ELECTROPHILIC AMINATION
ALS HETEROBESTANDTEILE
DERIVATIVES
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Summary:Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydrazino acids derived from 19 out of the 20 canonical proteinogenic amino acids and demonstrate their use in the solid-phase synthesis of N-amino peptide derivatives.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b02718