Different conformations of 1-deazaadenosine and its 2 `-deoxyribonucleoside in the solid state and in solution
DC Element | Wert | Sprache |
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dc.contributor.author | Seela, F | |
dc.contributor.author | Debelak, H | |
dc.contributor.author | Reuter, H | |
dc.contributor.author | Kastner, G | |
dc.contributor.author | Mikhailopulo, IA | |
dc.date.accessioned | 2021-12-23T16:03:38Z | - |
dc.date.available | 2021-12-23T16:03:38Z | - |
dc.date.issued | 1999 | |
dc.identifier.issn | 00404020 | |
dc.identifier.uri | https://osnascholar.ub.uni-osnabrueck.de/handle/unios/6108 | - |
dc.description.abstract | Crystallization of 1-deaza-2'-deoxyadenosine (c(1)A(d), 1) from propanol-2 gives two forms of crystals: type A formed firstly as plates, then, on the surface of the plates, type B appeared as needles. Single crystal X-ray analyses shows that the crystals A and B differ mainly in the sugar ring conformation: A adopts the S-type (P = 179.8 degrees; C-2'-endo-C-3'-exo; T-2(3)) conformation associated with an high-anti base orientation (chi = -90.7 degrees) and the gamma = 152.3 degrees across the exocyclic C(4')-C(5') bond; B shows N-type (P = 21.2; C-3'-endo; E-3) conformation accompanied by a somewhat different anti base orientation (chi = -116.5 degrees) an eclipsed orientation of the exocyclic C(4')-C(5') bond (gamma = 84.5 degrees). No intramolecular hydrogen bonds in both types of crystals can be detected. Unlike c(1)A(d), the ribonucleoside (c(1)A, 2) is in the syn conformation (chi = 56.1 degrees) in the solid state which is caused by an intramolecular (5')CH2OH ... N(3) hydrogen bond. The compounds 1 and 2 display very similar conformation in D2O solution with a strong preference for the S-type conformation of the furanose ring accompanied by the intramolecular (5')CH2OH ... N(3) hydrogen bond. (C) 1999 Published by Elsevier Science Ltd. All rights reserved. | |
dc.language.iso | en | |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | |
dc.relation.ispartof | TETRAHEDRON | |
dc.subject | 1-deaza-2 `-deoxyadenosine | |
dc.subject | 1-DEAZA-2'-DEOXYADENOSINE | |
dc.subject | 1-deazaadenosine | |
dc.subject | ADENOSINE-DEAMINASE | |
dc.subject | ANALOGS | |
dc.subject | Chemistry | |
dc.subject | Chemistry, Organic | |
dc.subject | conformation | |
dc.subject | HOOGSTEEN-DUPLEX DNA | |
dc.subject | MAGNETIC-RESONANCE | |
dc.subject | NUCLEOSIDES | |
dc.subject | NUCLEOTIDES | |
dc.subject | PENTOFURANOSE MOIETY | |
dc.subject | PROTON COUPLING-CONSTANTS | |
dc.subject | PSEUDOROTATIONAL EQUILIBRIUM | |
dc.subject | X-ray crystal structures | |
dc.title | Different conformations of 1-deazaadenosine and its 2 `-deoxyribonucleoside in the solid state and in solution | |
dc.type | journal article | |
dc.identifier.doi | 10.1016/S0040-4020(98)01131-4 | |
dc.identifier.isi | ISI:000078214900006 | |
dc.description.volume | 55 | |
dc.description.issue | 5 | |
dc.description.startpage | 1295 | |
dc.description.endpage | 1308 | |
dc.contributor.researcherid | H-9847-2014 | |
dc.publisher.place | THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND | |
dcterms.isPartOf.abbreviation | Tetrahedron | |
crisitem.author.dept | Institut für Chemie neuer Materialien | - |
crisitem.author.deptid | institute11 | - |
crisitem.author.parentorg | FB 05 - Biologie/Chemie | - |
crisitem.author.grandparentorg | Universität Osnabrück | - |
crisitem.author.netid | ReHa636 | - |
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geprüft am 01.06.2024