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7‐Nitro‐7‐deaza‐2′‐deoxyadenosine and 8‐Methyl‐7‐deaza‐2′‐deoxyguanosine: Pyrrolo[2,3‐ d ]pyrimidine Nucleosides with Different Sugar Conformations
Author(s) -
Seela Frank,
Rosemeyer Helmut,
Zulauf Matthias,
Chen Yaoming,
Kastner Guido,
Reuter Hans
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971215
Subject(s) - chemistry , deoxyadenosine , pyrimidine , stereochemistry , deoxyguanosine , nitro , alkane stereochemistry , sugar , crystal structure , crystallography , dna , organic chemistry , biochemistry , alkyl
The crystal structures of 7‐nitro‐7‐deaza‐2′ ‐deoxyadenosine ( 3 ) and 8‐methyl‐7‐deaza‐2′ ‐deoxyguanosine ( 5 ) have been determined and were compared with those of the parent 7‐deaza‐2′ ‐deoxyadenosine ( 2 ) and other 7‐substituted 7‐deazapurine 2′ ‐deoxynucleosides 4 and 6 . The sugar pucker of compound 3 is N ( 3′ T 2′ ) whereas compound 5 shows 2′ E conformation (S‐type). Despite the methyl group, compound 5 exhibits anti conformation about the N ‐glycosylic bond as in all other cases. The predominant conformations of 3 and 5 in aqueous solution, determined by 1 H NMR spectroscopy, is consistent with those in the solid state.