PMID- 29314327
OWN - NLM
STAT- MEDLINE
DCOM- 20180406
LR  - 20180406
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 24
IP  - 11
DP  - 2018 Feb 21
TI  - Sialyl Tn Unit with TFA-Labile Protection Realizes Efficient Synthesis of Sialyl 
      Glycoprotein.
PG  - 2593-2597
LID - 10.1002/chem.201706127 [doi]
AB  - Amino acids bearing 4-methylbenzyl (MBn) and 4-methoxybenzyl (MPM)-protected 
      sialic acid were synthesized and used for the 9-fluorenylmethoxycarbonyl (Fmoc) 
      solid-phase synthesis of a glycopeptide. The alpha-sialyl linkage of the 
      MBn-protected unit was partially cleaved under the final deprotection by 
      trifluoroacetic acid (TFA). In addition, the removal of several MBn groups were 
      incomplete. On the other hand, the MPM-protected unit gave the desired 
      glycopeptide without decomposition of the alpha-sialyl linkage. Using this unit, 
      peptide thioesters of the tandem repeat unit of MUC1 mucin were synthesized by 
      the N-alkylcysteine (NAC) method and used for the one-pot ligation by the 
      thioester method. As a result, the three tandem repeats of MUC1 carrying sialyl 
      Tn antigens were successfully synthesized.
CI  - (c) 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Takeda, Naoki
AU  - Takeda N
AD  - Institute for Protein Research, Osaka University, Osaka, 565-0871, Japan.
FAU - Takei, Toshiki
AU  - Takei T
AD  - Institute for Protein Research, Osaka University, Osaka, 565-0871, Japan.
FAU - Asahina, Yuya
AU  - Asahina Y
AD  - Institute for Protein Research, Osaka University, Osaka, 565-0871, Japan.
FAU - Hojo, Hironobu
AU  - Hojo H
AD  - Institute for Protein Research, Osaka University, Osaka, 565-0871, Japan.
LA  - eng
PT  - Journal Article
DEP - 20180125
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (9-fluorenylmethoxycarbonyl)
RN  - 0 (Fluorenes)
RN  - 0 (Glycopeptides)
RN  - 0 (sialyl-Tn-MUC1)
RN  - E5R8Z4G708 (Trifluoroacetic Acid)
RN  - GZP2782OP0 (N-Acetylneuraminic Acid)
SB  - IM
MH  - Fluorenes/chemistry
MH  - Glycopeptides/chemical synthesis/*chemistry
MH  - N-Acetylneuraminic Acid/chemistry
MH  - Solid-Phase Synthesis Techniques
MH  - Trifluoroacetic Acid/chemistry
OTO - NOTNLM
OT  - benzyl protection
OT  - carbohydrates
OT  - ligation method
OT  - peptide thioester
OT  - sialic acid
EDAT- 2018/01/10 06:00
MHDA- 2018/04/07 06:00
CRDT- 2018/01/10 06:00
PHST- 2017/12/26 00:00 [received]
PHST- 2018/01/10 06:00 [pubmed]
PHST- 2018/04/07 06:00 [medline]
PHST- 2018/01/10 06:00 [entrez]
AID - 10.1002/chem.201706127 [doi]
PST - ppublish
SO  - Chemistry. 2018 Feb 21;24(11):2593-2597. doi: 10.1002/chem.201706127. Epub 2018 
      Jan 25.