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

doi:10.1016/0006-291X(70)90764-3

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 journal › Article › peer-review

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 language	English (US)
Pages (from-to)	110-113
Number of pages	4
Journal	Biochemical and biophysical research communications
Volume	39
Issue number	1
DOIs	https://doi.org/10.1016/0006-291X(70)90764-3
State	Published - Apr 8 1970
Externally published	Yes

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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title = "Synthesis and relationship of L-glutaminyl-L-histidyl-L-prolinamide to the thyrotropin releasing hormone",

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.",

author = "Karl Folkers and Chang, {Jaw Kang} and Currie, {Bruce L.} and Bowers, {C. Y.} and Alice Weil and Schally, {A. V.}",

year = "1970",

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AU - Folkers, Karl

AU - Chang, Jaw Kang

AU - Currie, Bruce L.

AU - Bowers, C. Y.

AU - Weil, Alice

AU - Schally, A. V.

PY - 1970/4/8

Y1 - 1970/4/8

N2 - 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.

AB - 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.

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