Synthesis and biological activity of a cyclic pseudohexapeptide analog of somatostatin

Thomas W. Gero; Arno F. Spatola; Ignacio Torres-Aleman; Andrew V. Schally

doi:10.1016/S0006-291X(84)80183-7

Synthesis and biological activity of a cyclic pseudohexapeptide analog of somatostatin

Thomas W. Gero, Arno F. Spatola, Ignacio Torres-Aleman, Andrew V. Schally

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

A cyclic pseudohexapeptide analog of somatostatin, cyclo(Pro[CH₂S]Phe-D- Trp-Lys-Thr-Phe) was synthesized by solid phase methods and diphenylphosphoryl azide ring closure. The resulting crystalline compound possessed 23% of the growth hormone inhibitory activity of the parent tetradecapeptide and approximately 6% of the activity of the all-amide cyclic hexapeptide analog inspite of the absence of one of the two postulated intramolecular hydrogen bonds.

Original language	English (US)
Pages (from-to)	840-845
Number of pages	6
Journal	Biochemical and biophysical research communications
Volume	120
Issue number	3
DOIs	https://doi.org/10.1016/S0006-291X(84)80183-7
State	Published - May 16 1984
Externally published	Yes

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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abstract = "A cyclic pseudohexapeptide analog of somatostatin, cyclo(Pro[CH2S]Phe-D- Trp-Lys-Thr-Phe) was synthesized by solid phase methods and diphenylphosphoryl azide ring closure. The resulting crystalline compound possessed 23% of the growth hormone inhibitory activity of the parent tetradecapeptide and approximately 6% of the activity of the all-amide cyclic hexapeptide analog inspite of the absence of one of the two postulated intramolecular hydrogen bonds.",

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AU - Gero, Thomas W.

AU - Spatola, Arno F.

AU - Torres-Aleman, Ignacio

AU - Schally, Andrew V.

PY - 1984/5/16

Y1 - 1984/5/16

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AB - A cyclic pseudohexapeptide analog of somatostatin, cyclo(Pro[CH2S]Phe-D- Trp-Lys-Thr-Phe) was synthesized by solid phase methods and diphenylphosphoryl azide ring closure. The resulting crystalline compound possessed 23% of the growth hormone inhibitory activity of the parent tetradecapeptide and approximately 6% of the activity of the all-amide cyclic hexapeptide analog inspite of the absence of one of the two postulated intramolecular hydrogen bonds.

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