Synthesis and relationship of L-glutaminyl-L-histidyl-L-prolinamide to the thyrotropin releasing hormone

Karl Folkers, Jaw Kang Chang, Bruce L. Currie, C. Y. Bowers, Alice Weil, A. V. Schally

Research output: Contribution to journalArticle

29 Scopus citations

Abstract

The new L-glutaminyl-L-histidyl-L-prolinamide (Gln-His-Pro(NH2)) has been synthesized. This open glutaminyl-form has been compared with the cyclized pyro-form of (pyro)Glu-His-Pro(NH2), thyrotropin releasing hormone (TRH). Gln-His-Pro(NH2) is converted into (pyro)Glu-His-Pro(NH2) under very mild conditions some of which are analogous to steps used in the isolation of TRH. Gln-His-Pro(NH2) had up to five per cent of the activity of TRH although it is unknown whether this activity is intrinsic or due to contamination or conversion. There is no evidence that Gln-His-Pro(NH2) is present in the hypothalamus, but if it were it could be a moiety of a larger molecule which is convertible into Gln- or (pyro)Glu-His-Pro(NH2) or it could be a biosynthetic precursor or a metabolic transformation product of TRH. (Pyro)Glu-His-Pro(NH2) shows the functions expected of the hormone.

Original languageEnglish (US)
Pages (from-to)110-113
Number of pages4
JournalBiochemical and biophysical research communications
Volume39
Issue number1
DOIs
StatePublished - Apr 8 1970
Externally publishedYes

ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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