TY - JOUR
T1 - Systematic syntheses and inhibitory activities of bisubstrate-type inhibitors of sialyltransferases
AU - Hinou, Hiroshi
AU - Sun, Xue
AU - Ito, Yukishige
PY - 2003/7/11
Y1 - 2003/7/11
N2 - Bisubstrate-type sialyltransferase inhibitors 1/2a-e, having CMP-NeuAc and N-acetyllactosamine (or lactose) moieties connected by an alkanedithiol linker, were synthesized systematically. A uniform synthetic strategy was adopted that consists of consecutive couplings of three components (N-acetyllactosamine or lactose, sialic acid, and CMP), followed by oxidation. Due to the sensitivity of the compounds under alkaline conditions, final deprotection required careful monitoring by 1H NMR. The inhibitory activities of 1/2a-e toward ST6N and ST3N indicated that both the structure of the acceptor moiety and the distance between donor and acceptor moieties were important.
AB - Bisubstrate-type sialyltransferase inhibitors 1/2a-e, having CMP-NeuAc and N-acetyllactosamine (or lactose) moieties connected by an alkanedithiol linker, were synthesized systematically. A uniform synthetic strategy was adopted that consists of consecutive couplings of three components (N-acetyllactosamine or lactose, sialic acid, and CMP), followed by oxidation. Due to the sensitivity of the compounds under alkaline conditions, final deprotection required careful monitoring by 1H NMR. The inhibitory activities of 1/2a-e toward ST6N and ST3N indicated that both the structure of the acceptor moiety and the distance between donor and acceptor moieties were important.
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U2 - 10.1021/jo030042g
DO - 10.1021/jo030042g
M3 - Article
C2 - 12839452
SN - 0022-3263
VL - 68
SP - 5602
EP - 5613
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -