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ID 115859
Author
Keywords
non-canonical amino acid derivative
peptide
α-amino phosphonic acid
hydrophobic anchor
recyclable organocatalyst
Content Type
Journal Article
Description
Non-canonical amino acid derivatives are an attractive scaffold for novel drug candidates. Among the methods used to prepare this motif, the asymmetric Mannich-type reaction of α-imino carboxylic acid derivatives is a preeminent strategy because a wide variety of non-canonical amino acids can be accessed by changing only the nucleophile. Preparing the common substrate is difficult, however, which makes this method problematic. We developed a convenient method for synthesizing common substrates using MnO2-mediated oxidation of stable precursors. Peptides bearing non-canonical amino acids are another attractive synthetic target. We propose a new approach for synthesizing non-canonical amino acid-containing peptides by directly applying various organic reactions to peptidic substrates. Using hydrophobic anchor-supported peptides, we directly applied ring-closing metathesis and asymmetric Friedel–Crafts reactions to peptidic substrates. We also developed a novel recyclable organocatalyst according to the nature of the hydrophobic anchor tagged compound.
Journal Title
Chemical and Pharmaceutical Bulletin
ISSN
00092363
13475223
NCID
AA00602100
Publisher
The Pharmaceutical Society of Japan
Volume
69
Issue
4
Start Page
303
End Page
313
Published Date
2021-04-01
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Publisher
departments
Pharmaceutical Sciences