Document Detail

An approach to the elucidation of metabolic breakdown products of the luteinizing hormone-releasing hormone.
MedLine Citation:
PMID:  7019446     Owner:  NLM     Status:  MEDLINE    
Metabolic breakdown of the luteinizing hormone-releasing hormone (LH-RH) could lead to the following fragments containing pyroglutamic acid: pyroglutamic acid (1), pGlu-His (2), pGLu-His-Trp (3), pGlu-His-Trp-Ser (4), etc., and finally pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly (10). We have synthesized fragments 2-10 and successfully separated all ten metabolites and LH-RH by high-performance liquid chromatography (HPLC) with a muBondapak C18 column. In a test of the viability of the method, cochromatography of fragments 1-10 and LH-RH with the products of chymotryptic digestion of tritiated LH-RH showed radioactive peaks corresponding to the expected products, fragments 3 and 5. Analysis of the products of incubation of a rat kidney homogenate supernatant with LH-RH showed fragments 1-4 and LH-RH. The finding of breakdown at position 4 uncovers a new site of LH-RH breakdown and points the way to the design of potential LH-RH antagonists and agonists where the 4 position would be substituted with unnatural amino acids to prevent breakdown.
M A Stetler-Stevenson; D C Yang; A Lipkowski; L McCartney; D Peterson; G Flouret
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of medicinal chemistry     Volume:  24     ISSN:  0022-2623     ISO Abbreviation:  J. Med. Chem.     Publication Date:  1981 Jun 
Date Detail:
Created Date:  1981-09-22     Completed Date:  1981-09-22     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  9716531     Medline TA:  J Med Chem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  688-92     Citation Subset:  IM    
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MeSH Terms
Chromatography, High Pressure Liquid
Gonadotropin-Releasing Hormone / chemical synthesis,  metabolism*
Kidney / metabolism
Peptide Fragments / chemical synthesis,  metabolism*
Pyrrolidonecarboxylic Acid / metabolism
Grant Support
Reg. No./Substance:
0/Peptide Fragments; 33515-09-2/Gonadotropin-Releasing Hormone; 98-79-3/Pyrrolidonecarboxylic Acid

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