Identification of a novel aminonucleoside produced by Enterobacter sp. as 2'-amino-2'-deoxyguanosine.

A Critical Appraisal of the Evolution ofN-Nitrosoureas as Anticancer Drugs

“…539 The low activity of these purine analogs could be explained 319 by an intramolecular cyclization involving the neighboring C3′-hydroxyl to form a cyclic urethane, in analogy to the mechanism of Scheme 17b. Furthermore, the 2′-amino-2′-deoxyguanosine (762) was reported 540 to be an antimetabo-lite which exhibited anticancer activity. Additional nucleoside derivatives 769 and 770 were synthesized.…”

Molecular orbital studies on nucleoside antibiotics, VII. Conformation of 2′-amino- 2′-deoxyguanosine

“…1), is isolated from Aerobacter (Nakanishi et al, 1974} and is one of the two naturally occurring nucleoside analogs of guanosine, the other being isoguanosine (crotonoside} (Suhadolnik, 1979}. This antibiotic shows antitumor activity against HeLa ceils and sarcoma 180 and also inhibits RNA and protein syntheses in E. coil KY 3591 (Nakanishi et al, 1974(Nakanishi et al, , 1976(Nakanishi et al, , 1977. We have investigated theoretically the conformational properties of this molecule as well as the parent nucleoside, guanosine, by the PCILO method as a part of our studies on nucleoside antibiotics (Saran et al, 1977;Saran and Mitra, 1979;Saran and Chatterjee, 1980;Chatterjee and Saran, 1981;Saran and Patniak, t981, 1982).…”

Synthesis of buchananine, a novel pyridine alkaloid

“…1,2-O-Isopropylidene-D-glucofuranose (2) was treated (Scheme I) with nicotinoyl chloride2 in pyridine and gave a 77% yield of l,2-0-isopropylidene-6-0-nicotinoyl-Dglucofuranose (3). Treatment of 3 with 5 N HC1, followed by a bicarbonate workup, then gave 6-O-nicotinoyl-Dpyranose (4) as a crystalline solid which was shown by 360-MHz NMR in D20 to be a 40:60 mixture of the a and ß isomers (Figure l).…”