SYNTHESIS OF [N-15]GUANOSINES AND DEOXY[N-15]GUANOSINES FROM 5-AMINO-1-(BETA-D-RIBOFURANOSYL)IMIDAZOLE-4-CARBOXAMIDE (AICA-RIBOSIDE)

被引：20

作者：

BLEASDALE, C ^{[1
]}

ELLWOOD, SB ^{[1
]}

GOLDING, BT ^{[1
]}

SLAICH, PK ^{[1
]}

TAYLOR, OJ ^{[1
]}

WATSON, WP ^{[1
]}

机构：

[1] SHELL RES LTD,SITTINGBOURNE RES CTR,SITTINGBOURNE ME9 8AG,KENT,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 19期

关键词：

D O I：

10.1039/p19940002859

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methods are described for the syntheses of N-15-labelled guanosines and deoxyguanosines suitable for incorporation into oligonucleotides. The N-15 is located either at N-1 (e.g. [N-15(1)]guanosine la and deoxy[N-15(1)]guanosine 1b) or at the NH2 (e.g. [(NH2)-N-15]guanosine 1c and deoxy[(NH2)-N-15]guanosine Id). One of the synthetic methods starts from 5-amino-1-(beta-D-ribofuranosyl) imidazole-4-carboxamide (AICA-riboside, 2a) and leads via a cyclonucleoside to mixtures of compounds 1a and 1c, in which either compound predominates depending on the source of N-15 (ammonia or benzoyl isothiocyanate). The other method utilises the same starting material, but a different mode of formation of the pyrimidine ring and yields either guanosine 1a or 1c (as its 2-N-benzoyl derivative 8b), exclusively.

引用

页码：2859 / 2865

页数：7

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