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Synthesis of 14 C‐labelled thyrotropin releasing hormone [pyroglutamylhistidyl‐ 14 C(U)‐prolineamide]
Author(s) -
Flouret George,
Alter Arthur,
Gendrich Ronald
Publication year - 1972
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590080107
Subject(s) - dipeptide , thyrotropin releasing hormone , yield (engineering) , histidine , chemistry , hormone , chromatography , stereochemistry , peptide , biochemistry , amino acid , materials science , metallurgy
Abstract A simplified synthesis of pyroglutamylhistidyl‐prolineamide (TRH) was developed for the purpose of making labelled TRH. Pentachlorophenyl pyroglutamate was reacted with histidine to make pyroglutamylhistidine, and the dipeptide was coupled in situ with prolineamide by means of dicyclohexylcarbodiimide to yield the desired hormone. Both the dipeptide and the hormone were purified by chromatography on silica gel. This method of synthesis was conveniently adapted to synthesize TRH‐ 14 C starting with histidine‐ 14 C (U). Purification of labelled TRH was accomplished by preparative TLC.