ID 111904
Author
Yamamoto, Jun The University of Tokushima
Nishioka, Naomi The University of Tokushima
Keywords
Asymmetric α-amination
Organocatalyst
Peptide bond cleavage
Stimulus-responsive
UV-responsive
Content Type
Journal Article
Description
Development of a methodology to control the function of peptides and proteins is an indispensable task in the field of chemical biology and drug delivery. Recently, we reported synthesis of racemic stimulus-responsive amino acids and their application for controlling peptidyl function. In this study, we report enantioselective synthesis of a key intermediate of stimulus-responsive amino acids via asymmetric α-amination reaction of an aldehyde. The obtained chiral intermediate was converted to an Fmoc protected UV-responsive amino acid with (S)-configuration, and it was successfully incorporated into a model peptide by Fmoc solid phase peptide synthesis.
Journal Title
Tetrahedron
ISSN
00404020
NCID
AA00861787
AA11539786
Publisher
Elsevier Ltd.
Volume
66
Issue
37
Start Page
7367
End Page
7372
Published Date
2010-07-21
Rights
© 2010. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences