Conformational studies on tocinamide and deaminotocinamide by 220 MHz nuclear magnetic resonance spectroscopy.

Proceedings of the National Academy of Sciences of the United States of America ·Vol. 69 ·No. 6 ·1972-06-00 ·Pages 1470-4

Brewster AI, Glasel JA, Hruby VJ

Abstract

The 220 MHz spectra of tocinamide and deaminotocinamide, the ring moieties of oxytocin and of deamino-oxytocin, respectively, were investigated in [U-(2)H]dimethylsulfoxide solution. Extensive decoupling and exchange experiments allow complete spectral assignment and determination of many coupling constants. Circular dichroism spectra assigned a right-hand screw sense to the C-S-S-C group. The conformations of tocinamide and deaminotocinamide are different from each other and from those suggested for the ring portions of oxytocin and deamino-oxytocin. The relationship of this difference to biological activity is commented upon. The importance of the interaction of the side chain with the ring in oxytocin and deamino-oxytocin is emphasized.

MeSH Terms

Chemical Phenomena Chemistry Circular Dichroism Deamination Deuterium Disulfides Magnetic Resonance Spectroscopy Models, Structural Oxytocin Peptides Peptides, Cyclic Protein Conformation Structure-Activity Relationship Temperature

Chemicals

Disulfides Peptides Peptides, Cyclic Oxytocin Deuterium

Authors & Affiliations

3 authors, click to expand affiliations / ORCID

Brewster A I

Glasel J A

Hruby V J

References (21)

21 references, click to expand

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Article Info

Journal

Proceedings of the National Academy of Sciences of the United States of America

Abbr.

Proc Natl Acad Sci U S A

ISSN

0027-8424

DOI

10.1073/pnas.69.6.1470

Published

1972-06-00

Pages

1470-4

Language

English

Region

United States

NLM ID

7505876

PMCID

PMC426728

Subset

External Links

PubMed source DOI: 10.1073/pnas.69.6.1470 PMC Full Text View journal details

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Conformational studies on tocinamide and deaminotocinamide by 220 MHz nuclear magnetic resonance spectroscopy.

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