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2, 5‐Diketopiperazines (Cyclic Dipeptides) in Beef: Identification, Synthesis, and Sensory Evaluation
Author(s) -
Chen M.Z.,
Dewis M.L.,
Kraut K.,
Merritt D.,
Reiber L.,
Trinnaman L.,
Da Costa N.C.
Publication year - 2009
Publication title -
journal of food science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 150
eISSN - 1750-3841
pISSN - 0022-1147
DOI - 10.1111/j.1750-3841.2009.01062.x
Subject(s) - diketopiperazines , identification (biology) , sensory system , chemistry , microbiology and biotechnology , biology , neuroscience , stereochemistry , botany
Stewed beef and grilled dry aged beef were analyzed as part of an in‐depth analytical program, with the aim of creating new flavors incorporating only compounds identified in the target foods and identifying new synthesis targets. In‐house GC‐MS analyses of several types of cooked beef have identified over 1000 volatile and semivolatile components; many for the 1st time. Among the semivolatiles detected were ten 2, 5‐diketopiperazines (cyclic dipeptides) previously unreported in beef. These cyclic dipeptides are cis ‐cyclo( l ‐Ile‐ l ‐Pro), cis ‐cyclo( l ‐Leu‐ l ‐Pro), cis ‐cyclo( l ‐Pro‐ l ‐Pro), cis ‐cyclo( l ‐Pro‐ l ‐Val), cis ‐cyclo( l ‐Ala‐ l ‐Pro), cyclo(Gly‐ l ‐Pro), cyclo(Gly‐ l ‐Leu), cis ‐cyclo( l ‐Met‐ l ‐Pro), cis ‐cyclo( l ‐Phe‐ l ‐Pro), and cis‐ cyclo( l ‐Phe‐ l ‐Val). All 10 cyclic dipeptides were synthesized and evaluated organoleptically. Among them cis ‐cyclo( l ‐Leu‐ l ‐Pro), cis ‐cyclo( l ‐Met‐ l ‐Pro), and cis ‐cyclo( l ‐Phe‐ l ‐Pro) were found to be of particular organoleptic interest.