PMID- 20449504
OWN - NLM
STAT- MEDLINE
DCOM- 20100730
LR  - 20100507
IS  - 1477-0539 (Electronic)
IS  - 1477-0520 (Linking)
VI  - 8
IP  - 8
DP  - 2010 Apr 21
TI  - Chemical synthesis of mouse pro-opiomelanocortin(1-74) by azido-protected 
      glycopeptide ligation via the thioester method.
PG  - 1966-72
LID - 10.1039/b927270d [doi]
AB  - The thioester method is a peptide condensation reaction, which requires the 
      protection of Lys side chains for chemoselective ligation. We recently found that 
      the azido group could be used as an amino protecting group in the peptide 
      condensation by the thioester method. In this study, we synthesized the 
      glycosylated mouse pro-opiomelanocortin (1-74) by the thioester method. The 
      N-terminal peptide thioester segment, whose Lys side chain was protected by an 
      azido group, was prepared using a 9-fluorenylmethoxycarbonyl (Fmoc) strategy and 
      an N-alkylcysteine (NAC)-assisted thioesterification reaction. The C-terminal 
      azido-glycopeptide segment carrying N- and O-linked glycans was also prepared by 
      the Fmoc chemistry and condensed with the N-terminal segment by the silver 
      ion-free thioester method. These results showed that our azido-based strategy was 
      fully compatible with the NAC-assisted method and glycoprotein synthesis.
FAU - Katayama, Hidekazu
AU  - Katayama H
AD  - Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 
      1117 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan. katay@hotmail.co.jp
FAU - Hojo, Hironobu
AU  - Hojo H
FAU - Shimizu, Ichiko
AU  - Shimizu I
FAU - Nakahara, Yuko
AU  - Nakahara Y
FAU - Nakahara, Yoshiaki
AU  - Nakahara Y
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Org Biomol Chem
JT  - Organic & biomolecular chemistry
JID - 101154995
RN  - 0 (Azides)
RN  - 0 (Glycopeptides)
RN  - 0 (Sulfhydryl Compounds)
RN  - 66796-54-1 (Pro-Opiomelanocortin)
SB  - IM
MH  - Amino Acid Sequence
MH  - Animals
MH  - Azides/chemical synthesis/chemistry
MH  - Glycopeptides/chemical synthesis/*chemistry
MH  - Mice
MH  - Molecular Sequence Data
MH  - Pro-Opiomelanocortin/*chemical synthesis/chemistry
MH  - Sulfhydryl Compounds/chemical synthesis/chemistry
EDAT- 2010/05/08 06:00
MHDA- 2010/07/31 06:00
CRDT- 2010/05/08 06:00
PHST- 2010/05/08 06:00 [entrez]
PHST- 2010/05/08 06:00 [pubmed]
PHST- 2010/07/31 06:00 [medline]
AID - 10.1039/b927270d [doi]
PST - ppublish
SO  - Org Biomol Chem. 2010 Apr 21;8(8):1966-72. doi: 10.1039/b927270d.