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Tetrahydrolipstatin: Degradation products produced by human carboxyl‐ester lipase
Author(s) -
Stalder Henri,
Oesterhelt Gottfried,
Borgström Bengt
Publication year - 1992
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19920750513
Subject(s) - chemistry , hydrolysis , lipase , serine , metabolite , degradation (telecommunications) , ring (chemistry) , stereochemistry , lactone , enzyme , biochemistry , organic chemistry , telecommunications , computer science
The fate of tetrahydrolipstatin ( 1 ) incubated with human carboxyl‐ester lipase (HCEL) was investigated. The primary metabolite was identified as δ‐( N ‐formyl‐ L ‐leucyloxy)‐β‐hydroxy acid 2a with conserved configuration. It is formed by attack of the active‐site serine of HCEL at the carbonyl C‐atom of the β‐lactone ring of 1 followed by hydrolysis of the intermediate serine ester. Further products isolated were identified and a complete degradation scheme is proposed.