Stereoselective nucleoside deuteration for NMR studies of DNA

Nucleosides, Nucleotides and Nucleic Acids

Volumn 29, Issue 7, 2010, Pages 562-573

  Lukin, Mark ^a   Santos, Carlos De Los ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

Deuterated nucleosides; DNA lesions; oligonucleotides; solution state NMR

Indexed keywords

DNA; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; PROTON; PYRIMIDINE DERIVATIVE;

ARTICLE; COMPARATIVE STUDY; EXPERIMENT; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

DEUTERIUM; DNA; DNA DAMAGE; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOSIDES; OXIDATION-REDUCTION; PROTONS; PYRIMIDINE NUCLEOSIDES; STEREOISOMERISM;

EID: 77954250845     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2010.494650     Document Type: Article

References (16)

1. Földesi, A.; Trifonova, A.; Kundu, M.K.; Chattopadhyaya, J. The synthesis of deuterionucleosides. nucleosides. Nucleotides and Nucleic Acids, 2000, 19, 10, 1615.
2. Cromsigt, J.; Schleucher, J.; Gustafsson, T.; Kihlberg, J.; Wijmenga, S. Preparation of partially 2H/13C-labelled RNA for NMR studies. Stereo-specific deuteration of the H5" in nucleotides. Nucl. Acids Res. 2002, 30, 1639.
3. Kawashima, E.; Toyama, K.; Ohshima, K.; Kainosho, M.; Kyogoku, Y.; Ishido, Y. Novel approach to diastereoselective synthesis of 2′-deoxy[5′-2H1]ribonucleoside derivatives by reduction of the corresponding 5′-O-acetyl-2′-deoxy-5′- phenylselenoribonucleoside derivatives with a Bu3Sn2H-Et3Bsystem. Chirality 1997, 9, 435.
4. Ono, A.; Ono, A.; Kainosho, M. Thymidine via stereoselective deuteration of a 5-oxoribose derivative Tetr . Lett. 1997, 38, 395.
5. Kundu, M.K.; Földesi, A.; Chattopadhyaya, J. Studies on the stereoselective synthesis of deuterated -ribose derivatives. Helv. Chim. Acta 2003, 86, 633.
6. Xu, L.; Price, N.P.J. Stereoselective synthesis of chirally deuterated (S)-D-(6-2H1)glucose. Carbohydrate Res. 2004, 1173.
7. Midland, M.M.; Asirwatham, G.; Cheng, J.C.; Miller, J.A.; Morell, L. Synthesis and conformational analysis of(6R)-[6-2H1]-1,2:3,4-Di-O- isopropylidene-.alpha.-D-galactopyranose. NMR andmolecular modeling studies. J. Org. Chem. 1994, 59, 4438.
8. Lukin, M.A.; Bushuev, V.N. Stereoselective 5′-monodeuterated ribonucleoside phosphoramidites as tools for conformational studies of RNA by the NMR approach. Nucleosides & Nucleotides 1999, 18, 1255.
9. Ichikawa, Y.; Kubota, H.; Fujita, K.;Okauchi, T.; Narasaka, K. Stereoselective beta-C-glycosylation and beta-S-glycosylation of 2-deoxyfuranose derivatives controlled by the 3-hydroxy group. Bull. Chem. Soc. Japan 1989, 62, 845.
10. Hoffer, M.; Dushinsky, R.; Fox, J.J. Simple synthesis of pyrimidine 2′-deoxy-ribonucleotides. J. Am. Chem. Soc. 1959, 81, 4112.
11. Hodge, R.P.; Brush, C.K.; Harris, C.M.; Harris, T.M. Synthesis of 1- and 1,2,2′-deuteriated deoxyribose and incorporation into deoxyribonucleosides. J. Org. Chem. 1991, 56, 1553.
12. Beaucage, S. Protocols for Oligonucleotides and Analogs: Synthesis and Properties; Agrawal, S., ed.; Humana Press Inc., Totowa, NJ, 1993.
13. Schmeiser, H.H.; Stiborova, M.; Arldt, V.M. Chemical and molecular basis of the carcinogenicity of Aristolochia plants. Curr. Opin. Drug. Discov. Devel. 2009, 12, 141.
14. The preliminary structure was obtained by nOe based restrainedminimization using semi-qualitative distance restrains obtained from 300 ms NOESY spectra.
15. Attaluri, S.; Bonala, R.R.; Yang, I.Y.; Lukin, M.A.; Wen, Y.; Grollman, A.P.; Moriya, M.; Iden, C.R.; Johnson, F. DNA adducts of aristolochic acid II: total synthesis and site-specific mutagenesis studies in mammalian cells. Nucleic Acids Res. 2010, 38, 339.
16. Lukin, M.; Zaliznyak, T.; de los Santos, C. in preparation.