Enzymatic synthesis of 2'-deoxyguanosine with nucleoside deoxyribosyltransferase-II.
Nucleoside deoxyribosyltransferase-II (NdRT-II) of Lactobacillus helveticus, which catalyzes the transfer of a glycosyl residue from a donor deoxyribonucleoside to an acceptor base, has a broad specificity for the acceptor bases. Six-substituted purines were found to be substrates as acceptor bases for NdRT-II. Using this property of the enzyme, we established a practical procedure for enzymatic synthesis of 2'-deoxyguanosine (dGuo), consisting of the transglycosylation from thymidine to 6-substituted purine (2-amino-6-chloropurine; ACP) instead of natural guanine and the conversion of 2-amino-6-chloropurine-2'-deoxyriboside (ACPdR) to dGuo with bacterial adenosine deaminase. Through the successive reactions, dGuo was synthesized in high yield.
Okuyama
Kiyoshi
K
Biochemicals Division, Yamasa Corporation, Choshi, Chiba 288-0056, Japan. okuyama@yamasa.com
Shibuya
Susumu
S
Hamamoto
Tomoki
T
Noguchi
Toshitada
T
D000243:Adenosine Deaminase / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D000818:Animals; D002417:Cattle; D002851:Chromatography, High Pressure Liquid; D003849:Deoxyguanosine / Q000138:chemical synthesis*; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics; D006868:Hydrolysis; D007422:Intestines / Q000201:enzymology; D007700:Kinetics; D010430:Pentosyltransferases / Q000737:chemistry* / Q000378:metabolism; D010957:Plasmids / Q000235:genetics; D013379:Substrate Specificity; D013936:Thymidine / Q000737:chemistry
D010430:Pentosyltransferases; C067995:nucleoside phosphorylase; C420226:nucleoside deoxyribosyltransferase II; D000243:Adenosine Deaminase; D003849:Deoxyguanosine; D013936:Thymidine