1-deaza-3 `-O-methyladenosine: A nucleoside with the syn-conformation in the solid state and in solution

DC FieldValueLanguage
dc.contributor.authorSeela, F
dc.contributor.authorDebelak, H
dc.contributor.authorReuter, H
dc.contributor.authorKastner, G
dc.contributor.authorMikhailopulo, IA
dc.date.accessioned2021-12-23T16:12:55Z-
dc.date.available2021-12-23T16:12:55Z-
dc.date.issued1998
dc.identifier.issn15257770
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/10328-
dc.description.abstractThe 2'-O-methyl (2) and the 3'-O-methyl (3) derivatives of 1-deazaadenosine (1) were prepared. Single crystal X-ray analysis as well as H-1 and C-13 NMR studies were performed on the 3'-O-methyl-1-deazaadenosine 3. In the solid state, the glycosyl torsion angle (chi = 64.7 degrees) is in the syn-range which is caused by an intramolecular (5')CH2OH ... N(3) hydrogen bond. The ribofuranose moiety adopts a E-2 (C-3'-exo; S) conformation and the orientation of the exocyclic C(4')-C(5') bond is sc (gamma((+)g)). The conformation in solution was found to be very similar to that in solid state. Whereas the 2'-O-methyl derivative of 1 is a strong inhibitor of adenosine deaminase the 3'-O-methyl derivative is neither inhibitor nor substrate.
dc.language.isoen
dc.publisherTAYLOR & FRANCIS INC
dc.relation.ispartofNUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS
dc.subject1-DEAZA-2'-DEOXYADENOSINE
dc.subject1-DEAZAADENOSINE ANALOGS
dc.subjectADENINE NUCLEOSIDES
dc.subjectADENOSINE-DEAMINASE
dc.subjectBiochemistry & Molecular Biology
dc.subjectCRYSTAL
dc.subjectHOOGSTEEN-DUPLEX DNA
dc.subjectMAGNETIC-RESONANCE
dc.subjectNUCLEOTIDES
dc.subjectPURINE NUCLEOSIDES
dc.subjectSPECTROSCOPY
dc.title1-deaza-3 `-O-methyladenosine: A nucleoside with the syn-conformation in the solid state and in solution
dc.typejournal article
dc.identifier.doi10.1080/07328319808004671
dc.identifier.isiISI:000072726000003
dc.description.volume17
dc.description.issue4
dc.description.startpage729
dc.description.endpage744
dc.contributor.researcheridH-9847-2014
dc.identifier.eissn15322335
dc.publisher.place530 WALNUT STREET, STE 850, PHILADELPHIA, PA 19106 USA
dcterms.isPartOf.abbreviationNucleosides Nucleotides Nucleic Acids
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidReHa636-
Show simple item record

Page view(s)

1
Last Week
0
Last month
0
checked on Apr 23, 2024

Google ScholarTM

Check

Altmetric