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Synthesis and Irradiation of Vitamin‐B 12 ‐Derived Complexes Incorporating Peripheral G⋅C Base Pairs
Author(s) -
Sun FangPing,
Darbre Tamis
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200209)85:9<3002::aid-hlca3002>3.0.co;2-b
Subject(s) - moiety , chemistry , cytosine , derivative (finance) , guanine , stereochemistry , acetylation , nucleotide , medicinal chemistry , dna , biochemistry , financial economics , economics , gene
Abstract The vitamin‐B 12 derivative 11 , incorporating a peripheral N 4 ‐acetylcytosine moiety, was alkylated under reductive conditions with 2‐(iodomethyl)‐2‐methylmonothiomalonate 8 bearing the complementary guanine moiety. The reaction yielded a mixture of vitamin‐B 12 ‐derived complexes with variations in the cytosine moiety: products 16 – 18 with a cytosine, a N 4 ‐acetylated cytosine, and a N 4 ‐acetylated reduced cytosine moiety were formed (see Scheme 5 ). The complexes were photolyzed in CHCl 3 /MeCN to yield the dimethylmalonate derivative 22 ( Scheme 6 ) but not the rearranged succinate, in contrast to the results obtained earlier with complexes incorporating the A⋅T base pair (see Scheme 1 ).