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. 1972 Jun;69(6):1470–1474. doi: 10.1073/pnas.69.6.1470

Conformational Studies on Tocinamide and Deaminotocinamide by 220 MHz Nuclear Magnetic Resonance Spectroscopy

Anne I Brewster 1, J A Glasel *, V J Hruby †
PMCID: PMC426728  PMID: 4504362

Abstract

The 220 MHz spectra of tocinamide and deaminotocinamide, the ring moieties of oxytocin and of deamino-oxytocin, respectively, were investigated in [U-2H]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.

Keywords: spin decoupling, isotope exchange, circular dichroism, ring, side chain

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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