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An NMR and conformational investigation of the trans–syn cyclobutane photodimers of dUpdT

✍ Scribed by Walter A. Tabaczynski; Danielle G. E. Lemaire; Béla P. Ruzsicska; James L. Alderfer

Publisher
Wiley (John Wiley & Sons)
Year
1999
Tongue
English
Weight
77 KB
Volume
50
Category
Article
ISSN
0006-3525

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✦ Synopsis

Both trans-syn cyclobutane-type photodimers of 2Ј-deoxyuridylyl (3Ј-5Ј) thymidine (dUpdT) were formed by deamination of the corresponding trans-syn cyclobutane photodimers of 2Ј-deoxycytidylyl (3Ј-5Ј) thymidine (dCpdT) and were examined by 1 H-, 13 C-, and 31 P-nmr spectroscopy. One-and two-dimensional nmr experiments provided a nearly complete assignment of the 1 H, 13 C, and 31 P resonances. Scalar and nuclear Overhauser effect contacts were used to determine the conformation of the deoxyribose rings, exocyclic bonds, cyclobutane rings, and glycosidic linkages. Isomer I (S-type class; CB Ϫ ; SYN-ANTI) and isomer II (N-type class; CB ϩ ; ANTI-SYN) exhibit markedly different conformational features. 31 P chemical shifts show that the relative flexibility is dUpdT Ͼ isomer II Ͼ isomer I. The conformations of these species are very similar to those of other previously examined trans-syn photodimers.

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