Skip to main content
SpringerLink
Log in

Structures of isopropylidene nucleoside derivatives: implications for ribose ring flexibility under external cyclic constraints

  • Published:
Proceedings of the Indian Academy of Sciences - Chemical Sciences Aims and scope Submit manuscript

Abstract

Crystal structures of six isopropylidene nucleoside derivatives are described. The results show that, under external cyclic constraints, the ribose assumes a variety of unusual conformations. In those compounds which possess a base-to-sugar cyclization through the C(4′) atom, the furanose pucker is predominantly C(4′)-endo, O(4′)-exo. The possible relevance of the sulphur geometry in two of the compounds to certain structural aspects of the action of the enzyme thymidylate synthetase is also pointed out.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Altona C and Sundaralingam M 1972J. Am. Chem. Soc. 94 8205

    Article  CAS  Google Scholar 

  • Bode J and Shenk M 1977Cryst. Struct. Commun. 6 645

    CAS  Google Scholar 

  • Bugg C E, Thomas J M, Sundaralingam M and Rao S T 1971Biopolymers 10 175

    Article  CAS  Google Scholar 

  • Delbaere L T J and James M N G 1974Acta Crystallogr. B30 1241

    Google Scholar 

  • Depmeier W, Engels J and Klaska K H 1977Acta Crystallogr. B33 2436

    CAS  Google Scholar 

  • Fujii S, Fujiwara T and Tomita K 1976Nucl. Acids Res. 3 1985

    CAS  Google Scholar 

  • Gautham N 1983X-ray crystallographic investigations on modified nucleosides, Ph.D. Thesis, Indian Institute of Science, Bangalore

    Google Scholar 

  • Gautham N, Narasinga Rao B N, Anil Kumar and Viswamitra M A 1984Curr. Sci. 53 71

    CAS  Google Scholar 

  • Gautham N, Ramakrishnan P, Seshadri T P, Viswamitra M A, Salisbury S A and Brown D M 1982Acta Crystallogr. B38 2707

    CAS  Google Scholar 

  • Gautham N, Seshadri T P and Viswamitra M A 1983aActa Crystallogr. C39 456

    CAS  Google Scholar 

  • Gautham N, Seshadri T P, Viswamitra M A and Salisbury S A 1983bActa Crystallogr. C39 459

    CAS  Google Scholar 

  • Gautham N, Seshadri T P, Viswamitra M A, Salisbury S A and Brown D M 1983cActa Crystallogr. C39 1389

    CAS  Google Scholar 

  • Katti S K, Seshadri T P and Viswamitra M A 1981Acta Crystallogr. B37 407

    CAS  Google Scholar 

  • Saenger W and Sheit K H 1970J. Mol. Biol. 50 153

    Article  CAS  Google Scholar 

  • Seshadri T P, Gautham N and Viswamitra MA 1983Acta Crystallogr. C39 1706

    CAS  Google Scholar 

  • Sprang S, Rohrer D C and Sundaralingam M 1978Acta Crystallogr. B34 2803

    CAS  Google Scholar 

  • Sundaralingam M 1973Quantum chemistry and biochemistry, Proc. Symp. Jerusalem (eds) E D Bergman and B Pullman (Jerusalem: Israel Acad. Sci. and Humanities) p. 417

    Google Scholar 

  • Suck D, Saenger W, Main P, Germain G and Declercq J P 1974Biochem. Biophys. Acta 361 257

    CAS  Google Scholar 

  • Suck D, Saenger W and Vorbruggen H 1972Nature (London) 235 333

    Article  CAS  Google Scholar 

  • Viswamitra M A 1983Cold Spring Harbour Symp. on Quant. Biol. 47 25

    Google Scholar 

  • Viswamitra M A, Kennard O, Jones P G, Sheldrick G M, Salisbury S, Falvello L and Shakked Z 1978Nature (London) 273 687

    Article  CAS  Google Scholar 

  • Yamagata Y, Fujii S, Fujiwara T, Tomita K and Ueda T 1980Acta Crystallogr. B36 339

    CAS  Google Scholar 

  • Yamagata Y, Fujii S, Fujiwara T, Tomita K and Ueda T 1981Biochem. Biophys. Acta 654 242

    CAS  Google Scholar 

  • Zussman J 1953Acta Crystallogr. 6 504

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Physics and ICMR Centre on Genetics and Cell Biology, Indian Institute of Science, 560012, Bangalore, India

    M. A. Viswamitra & N. Gautham

Authors
  1. M. A. Viswamitra
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. Gautham
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Viswamitra, M.A., Gautham, N. Structures of isopropylidene nucleoside derivatives: implications for ribose ring flexibility under external cyclic constraints. Proc. Indian Acad. Sci. (Chem. Sci.) 93, 261–269 (1984). https://doi.org/10.1007/BF02840518

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02840518

Keywords

Search

Navigation