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ID 115115
Author
Kobayashi, Daishiro Tokushima University
Naruse, Naoto Tokushima University
Shigenaga, Akira Tokushima University|Fukuyama University KAKEN Search Researchers
Content Type
Journal Article
Description
Ring-opening by CuSO4 of a 1,3-thiazolidine carbonyl structure (Thz) as an N-terminal cysteine (Cys) residue revealed that an intramolecular S–acetamidomethyl cysteine (Cys(Acm)) can also be deprotected with concomitant formation of a disulphide bond connecting the two Cys residues. A mechanistic study on the disulphide formation led to a general protocol for deprotection of the S-Acm group by CuSO4 and a 1,2-aminothiol under aerobic conditions. Application of this new deprotection reaction allowed for the synthesis of Apamin, a peptide with two-disulphides in a one-pot/stepwise disulphide-bridging procedure.
Journal Title
Organic & Biomolecular Chemistry
ISSN
14770539
NCID
AA12084375
Publisher
The Royal Society of Chemistry
Volume
18
Issue
42
Start Page
8638
End Page
8645
Published Date
2020-08-20
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences