Study on highly diastereoselective synthesis of (2'R)-2'-deoxy[2'-2H]guanosine.
To develop an efficient method for the synthesis of a highly diasteroselective (2'R)-2'-deoxy[2'-2H]guanosine (1), studies of organic chemical conversion from 2'-bromo-2'-deoxy-N2-Isobutyryl-3',5'-O-TIPDS-guanosine (2) to 1 and a biological transdeoxyribofuranosylation of (2'R > 98% de)-2'-deoxy[2'-2H]uridine (4) were carried out. As the results, a highly diastereoselective synthesis of 1 was achieved by a biological transdeoxyribofuranosylation between 2,6-diaminopurine and 4 by the use of Enterobacter aerogenes AJ-11125, followed by treatment with adenosine deaminase. The results will be described in detail.
Kawashima
E
E
School of Pharmacy, Tokyo University of Pharmacy and Life Science.
Terui
Y S
YS
Ishido
Y
Y
Yokozeki
K
K
D000243:Adenosine Deaminase / Q000378:metabolism; D003849:Deoxyguanosine / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D003903:Deuterium / Q000737:chemistry; D021902:Enterobacter aerogenes / Q000378:metabolism; D006031:Glycosylation; D013237:Stereoisomerism
D003903:Deuterium; D000243:Adenosine Deaminase; D003849:Deoxyguanosine