PMID- 18642828
OWN - NLM
STAT- MEDLINE
DCOM- 20081020
LR  - 20131121
IS  - 1523-7052 (Electronic)
IS  - 1523-7052 (Linking)
VI  - 10
IP  - 16
DP  - 2008 Aug 21
TI  - Efficient sequential segment coupling using N-alkylcysteine-assisted 
      thioesterification for glycopeptide dendrimer synthesis.
PG  - 3531-3
LID - 10.1021/ol801340m [doi]
AB  - A highly pure MUC1-derived glycopeptide dendrimer of 22 kDa was prepared by a 
      sequential segment coupling, achieved by an N-alkylcysteine (NAC)-assisted 
      thioesterification. The glycopeptide having C-terminal NAC was prepared by the 
      Fmoc method and converted to the thioester by 3-mercaptopropionic acid treatment. 
      The thioester was condensed with a lysine trimer carrying NAC to afford tetramer, 
      which was then converted to the thioester. Two tetramers were condensed with 
      ethylenediamine to give the octameric glycopeptide dendrimer.
FAU - Ozawa, Chinatsu
AU  - Ozawa C
AD  - Department of Applied Biochemistry, Institute of Glycotechnology, Tokai 
      University, Kanagawa 259-1292, Japan.
FAU - Katayama, Hidekazu
AU  - Katayama H
FAU - Hojo, Hironobu
AU  - Hojo H
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
DEP - 20080719
PL  - United States
TA  - Org Lett
JT  - Organic letters
JID - 100890393
RN  - 0 (Dendrimers)
RN  - 0 (Esters)
RN  - 0 (Glycopeptides)
RN  - 0 (Sulfhydryl Compounds)
RN  - K848JZ4886 (Cysteine)
SB  - IM
MH  - Carbohydrate Conformation
MH  - Carbohydrate Sequence
MH  - Cysteine/*analogs & derivatives/*chemistry
MH  - Dendrimers/*chemical synthesis/chemistry
MH  - Esters/*chemistry
MH  - Glycopeptides/*chemical synthesis/chemistry
MH  - Molecular Sequence Data
MH  - Sulfhydryl Compounds/*chemistry
EDAT- 2008/07/23 09:00
MHDA- 2008/10/22 09:00
CRDT- 2008/07/23 09:00
PHST- 2008/07/23 09:00 [pubmed]
PHST- 2008/10/22 09:00 [medline]
PHST- 2008/07/23 09:00 [entrez]
AID - 10.1021/ol801340m [doi]
PST - ppublish
SO  - Org Lett. 2008 Aug 21;10(16):3531-3. doi: 10.1021/ol801340m. Epub 2008 Jul 19.