In:
Journal of Labelled Compounds and Radiopharmaceuticals, Wiley, Vol. 46, No. 14 ( 2003-12), p. 1269-1277
Abstract:
3,7,8‐ 15 N 3 ‐N 1 ‐( β ‐D‐ erythro ‐pentofuranosyl)‐5‐guanidinohydantoin was synthesized from the oxidation of 1,7,NH 2 ‐ 15 N 3 ‐8‐oxo‐7,8‐dihydro‐2′‐deoxyguanosine with 2 equivalents of Ir(IV) in pH 4.5 potassium phosphate buffer. The synthesis of 1,7,NH 2 ‐ 15 N 3 ‐8‐oxo‐7,8‐dihydro‐2′‐deoxyguanosine started with bromination of 1,7,NH 2 ‐ 15 N 3 ‐2′‐deoxyguanosine. The resulting 1,7,NH 2 ‐ 15 N 3 ‐8‐bromo‐7,8‐dihydro‐2′‐deoxyguanosine reacted with sodium benzyloxide to afford 1,7,NH 2 ‐ 15 N 3 ‐8‐benzyloxy‐7,8‐dihydro‐2′‐deoxyguanosine. Subsequent catalytic transfer hydrogenation of 1,7,NH 2 ‐ 15 N 3 ‐8‐benzyloxy‐7,8‐dihydro‐2′‐deoxyguanosine with cyclohexene and 10% Pd/C yielded 1,7,NH 2 ‐ 15 N 3 ‐8‐oxo‐7,8‐dihydro‐2′‐deoxyguanosine. Purification of 3,7,8‐ 15 N 3 ‐N 1 ‐( β ‐D‐ erythro ‐pentofuranosyl)‐5‐guanidinohydantoin was first carried out on a C18 column and the product was further purified on a graphite column. ESI‐MS was used to confirm the identity and to determine the isotopic purity of all the labeled compounds. The isotopic purity of 3,7,8‐ 15 N 3 ‐N 1 ‐( β ‐D‐ erythro ‐pentofuranosyl)‐5‐guanidinohydantoin was 99.4 atom% based on LC‐MS measurements. Copyright © 2003 John Wiley & Sons, Ltd.
Type of Medium:
Online Resource
ISSN:
0362-4803
,
1099-1344
Language:
English
Publisher:
Wiley
Publication Date:
2003
detail.hit.zdb_id:
1491841-9
detail.hit.zdb_id:
196095-7
SSG:
15,3
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