FTIR study on nucleotide analogues .1. Spectral characterization of dinucleoside methylphosphonates and dinucleoside 5'-methylenephosphonates in solution and in solid phase

被引:6
作者
Kulinska, K [1 ]
Sarzynska, J [1 ]
Szabo, T [1 ]
Stawinski, J [1 ]
机构
[1] UNIV STOCKHOLM,ARRHENIUS LAB,DEPT ORGAN CHEM,S-10691 STOCKHOLM,SWEDEN
关键词
D O I
10.1080/07391102.1997.10508951
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Some conformational feature of dithymidine nucleotides containing natural 3' -> 5' phosphodiester, methylphosphonate, or 5'-methylenephosphonate internucleotidic linkages were probed in solution and in solid phase using FTIR spectroscopy. A high similarity of the IR spectra in the region of 1800-1250 cm(-1) indicates that all the investigated compounds have similar glycosidic torsion angels and the preferred conformation of the deoxyribose rings. However, small but significant differences between the R-P and S-P diastereomers of methylphosphonate analogue 5 may suggest that the association or the hydration mode of these compounds may vary.
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页码:119 / 128
页数:10
相关论文
共 29 条
[1]   OLIGODEOXYRIBONUCLEOSIDE METHYLPHOSPHONATES - NMR AND UV SPECTROSCOPIC STUDIES OF RP-RP AND SP-SP METHYLPHOSPHONATE (ME) MODIFIED DUPLEXES OF (D[GGAATTCC])2 [J].
BOWER, M ;
SUMMERS, MF ;
POWELL, C ;
SHINOZUKA, K ;
REGAN, JB ;
ZON, G ;
WILSON, WD .
NUCLEIC ACIDS RESEARCH, 1987, 15 (12) :4915-4930
[2]   B-DNA TO Z-DNA TRANSITION PROBED BY OLIGONUCLEOTIDES CONTAINING METHYLPHOSPHONATES [J].
CALLAHAN, L ;
HAN, FS ;
WATT, W ;
DUCHAMP, D ;
KEZDY, FJ ;
AGARWAL, K .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (06) :1617-1621
[3]   MOLECULAR-STRUCTURE OF A DEOXYRIBOSE-DINUCLEOTIDE, SODIUM THYMIDYLYL-(5'-]3')-THYMIDYLATE-(5') HYDRATE (PTPT), AND A POSSIBLE STRUCTURAL MODEL FOR POLYTHYMIDYLATE [J].
CAMERMAN, N ;
FAWCETT, JK ;
CAMERMAN, A .
JOURNAL OF MOLECULAR BIOLOGY, 1976, 107 (04) :601-621
[4]   PHOTOCHEMISTRY OF DI(DEOXYRIBONUCLEOSIDE) METHYLPHOSPHONATES CONTAINING N-3-METHYL-4-THIOTHYMINE [J].
CLIVIO, P ;
FOURREY, JL ;
SZABO, T ;
STAWINSKI, J .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7273-7283
[5]   DESIGNING ANTISENSE OLIGONUCLEOTIDES AS PHARMACEUTICAL AGENTS [J].
COHEN, JS .
TRENDS IN PHARMACOLOGICAL SCIENCES, 1989, 10 (11) :435-437
[6]   The C-H center dot center dot center dot O hydrogen bond: Structural implications and supramolecular design [J].
Desiraju, GR .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (09) :441-449
[7]   INTERPRETATION OF DNA VIBRATION MODES .3. THE BEHAVIOR OF THE SUGAR PUCKER VIBRATION MODES AS A FUNCTION OF ITS PSEUDOROTATION PARAMETERS [J].
DOHY, D ;
GHOMI, M ;
TAILLANDIER, E .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1989, 6 (04) :741-754
[8]   SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION [J].
DUEHOLM, KL ;
EGHOLM, M ;
BEHRENS, C ;
CHRISTENSEN, L ;
HANSEN, HF ;
VULPIUS, T ;
PETERSEN, KH ;
BERG, RH ;
NIELSEN, PE ;
BUCHARDT, O .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5767-5773
[9]   CHEMICALLY MODIFIED OLIGONUCLEOTIDES AS PROBES AND INHIBITORS [J].
ENGLISCH, U ;
GAUSS, DH .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (06) :613-629
[10]  
HARVEY JC, 1992, SCIENCE, V258, P1481