TY - JOUR
T1 - Synthesis of an ether-linked alkyl 5a-carba-β-D-glucoside, a 5a-carba-β-D-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-D-glucoside, and an alkyl 5a′-carba-β-lactoside
AU - Ogawa, Seiichiro
AU - Aoyama, Hiroshi
AU - Sato, Toshinori
N1 - Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2002/11/19
Y1 - 2002/11/19
N2 - For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.
AB - For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-β-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine), in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-β-D-galactose residue into the 4-position of dodecyl β-D-glucopyranoside. A strong and specific inhibition of β-galactosidase (Ki 0.67 μM, bovine liver) was found for dodecyl 5a-carba-β-D-galactopyranoside.
KW - Alkyl 5a-carba-glycosides, ether-linked
KW - Biocombinatorial synthesis using a living cell
KW - Carba-sugars
KW - Sugar mimics
KW - β-Galactosidase inhibitor
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U2 - 10.1016/S0008-6215(02)00294-X
DO - 10.1016/S0008-6215(02)00294-X
M3 - Article
C2 - 12433463
AN - SCOPUS:0037137261
VL - 337
SP - 1979
EP - 1992
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
IS - 21-23
ER -