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Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1969 Sep;64(1):263–266. doi: 10.1073/pnas.64.1.263

DEUTERATED OXYTOCINS: THE SYNTHESIS AND BIOLOGICAL PROPERTIES OF A CRYSTALLINE ANALOG OF DEAMINO-OXYTOCIN DEUTERATED IN THE 5-ASPARAGINE POSITION*

Alfred T Blomquist 1,2,, Daniel H Rich 1,2, Bruce A Carlson 1,2, G Ashley Allen 1,2,, Victor J Hruby 1,2, Herbert Takashima 1,2, Louis L Nangeroni 1,2,§, Paula Glose 1,2, Vincent Du Vigneaud 1,2,
PMCID: PMC286156  PMID: 5263009

Abstract

This paper describes the synthesis and biological activity of [5-L-asparagine-α,β,β-d3]-deamino-oxytocin. The model peptide S-benzyl-β-mercaptopropionyl-L- asparaginyl-α,β,β-d3-glycinamide was also prepared to observe the effect of the conditions of peptide synthesis on the deuterium content. It was found that normal synthetic procedures could be used without a significant loss in the deuterium content.

The [5-L-asparagine-α,β,β-d3]-deamino-oxytocin had, within experimental error, the same avian vasodepressor and oxytocic activities as deamino-oxytocin itself.

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Selected References

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

  1. Blomquist A. T., Hiscock B. F., Harpp D. N. Deuterated amino acids. 3. Synthesis of DL-Aspartic-2,3,3-d-3 acid, L-glutamic-2,3,3,4,4-d-5 acid, L-asparagine-2,3,3-d-3, and L-Glutamine-2,3,3,4,4-d-5 1,2a. J Org Chem. 1966 Dec;31(12):4121–4127. doi: 10.1021/jo01350a058. [DOI] [PubMed] [Google Scholar]
  2. Blomquist A. T., Rich D. H., Hruby V. J., Nangeroni L. L., Glose P., Du Vigneaud V. Deuterated oxytocins: the synthesis and biological properties of three crystalline analogs of deamino-oxytocin deuterated in the 1-beta-mercaptopropionic acid position. Proc Natl Acad Sci U S A. 1968 Oct;61(2):688–692. doi: 10.1073/pnas.61.2.688. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. DUVIGNEAUD V., DENNING G. S., Jr, DRABAREK S., CHAN W. Y. THE SYNTHESIS AND PHARMACOLOGICAL STUDY OF 4-DECARBOXAMIDO-OXYTOCIN (4-ALPHA-AMINOBUTYRIC ACID-OXYTOCIN) AND 5-DECARBOXAMIDO-OXYTOCIN (5-ALANINE-OXYTOCIN). J Biol Chem. 1964 Feb;239:472–478. [PubMed] [Google Scholar]
  4. Ferrier B. M., Jarvis D., Du Vigneaud V. Deamino-oxytocin. Its isolation by partition chromatography on Sephadex and crystallization from water, and its biological activities. J Biol Chem. 1965 Nov;240(11):4264–4266. [PubMed] [Google Scholar]
  5. HOPE D. B., MURTI V. V., DU VIGNEAUD V. A highly potent analogue of oxytocin, desamino-oxytocin. J Biol Chem. 1962 May;237:1563–1566. [PubMed] [Google Scholar]
  6. MUNSICK R. A. Effect of magnesium ion on the response of the rat uterus to neurohypophysial hormones and analogues. Endocrinology. 1960 Mar;6:451–457. doi: 10.1210/endo-66-3-451. [DOI] [PubMed] [Google Scholar]
  7. PORATH J., FLODIN P. Gel filtration: a method for desalting and group separation. Nature. 1959 Jun 13;183(4676):1657–1659. doi: 10.1038/1831657a0. [DOI] [PubMed] [Google Scholar]
  8. Schild H. O. A method of conducting a biological assay on a preparation giving repeated graded responses illustrated by the estimation of histamine. J Physiol. 1942 Jun 2;101(1):115–130. doi: 10.1113/jphysiol.1942.sp003970. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. YAMASHIRO D. PARTITION CHROMATOGRAPHY OF OXYTOCIN ON 'SEPHADEX'. Nature. 1964 Jan 4;201:76–77. doi: 10.1038/201076a0. [DOI] [PubMed] [Google Scholar]

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