Volume 29, Issue 11
Natural Products
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ChemInform Abstract: 7-Nitro-7-deaza-2′-deoxyadenosine and 8-Methyl-7-deaza-2′-deoxyguanosine: Pyrrolo[2,3-d]pyrimidine Nucleosides with Different Sugar Conformations.

F. SEELA

F. SEELA

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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H. ROSEMEYER

H. ROSEMEYER

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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M. ZULAUF

M. ZULAUF

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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Y. CHEN

Y. CHEN

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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G. KASTNER

G. KASTNER

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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H. REUTER

H. REUTER

Lab. Org. Bioorg. Chem., Inst. Chem., Univ. Osnabrueck, D-49069 Osnabrueck, Germany

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First published: 23 June 2010

Abstract

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ChemInform Abstract

Based on 1H NMR spectroscopy and X-ray analysis it is found that the 7-nitro compound (II) adopts N-type sugar puckering conformation, whereas the 8-methylguanosine (III) shows S-type conformation. Despite the bulky methyl group in position 8, (III) exhibits anti conformation about the N-glycosylic bond.

chemical structure image

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