First Synthesis of a Representative, Natural Pterin Glycoside: 2′-O-(α-D-Glucopyranosyl) biopterin

被引:0
作者
Hanaya, Tadashi [1 ]
Yamamoto, Hiroshi [2 ]
Pfleiderer, Wolfgang [3 ]
机构
[1] Okayama Univ, Fac Sci, Dept Chem, Okayama 7008530, Japan
[2] Shujitsu Univ, Sch Pharm, Okayama 7038516, Japan
[3] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
关键词
biopterin D-glucoside; pterin glycoside; glycosylation; protecting groups; SYNECHOCOCCUS SP PCC-7942; EFFICIENT SYNTHESIS; TEPIDOPTERIN; PTERIDINES; LIMIPTERIN; GLUCOSIDE;
D O I
暂无
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Glycosylation of N(2)-(N, N-dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl) ethyl] biopterin (14) with the novel donor 4,6-di-O-acetyl-2,3-di-O-(4-methoxy-benzyl)-alpha-D- -glucopyranosyl bromide (19) in the presence of silver triflate and tetramethylurea predominantly afforded the corresponding a-D-glucopyranoside (20a), from which 2'-O-(alpha-D-glucopyranosyl) biopterin (1) was obtained by the successive removal of the protecting groups.
引用
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页码:36 / 41
页数:6
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