Lipase specificity toward some acetylenic and olefinic alcohols in the esterification of pentanoic and stearic acids

The esterification of five medium‐ and long‐chain acetylenic alcohols (2‐nonyn‐1‐ol, 10‐undecyn‐1‐ol, 6‐octadecyn‐1‐ol, 9‐octadecyn‐1‐ol, and 13‐docosyn‐1‐ol), seven olefinic alcohols (cis‐3‐nonen‐1‐ol, 10‐undecen‐1‐ol, cis‐6‐octadecen‐1‐ol, cis‐9‐octadecen‐1‐ol, trans‐9‐octadecen‐1‐ol, trans‐9, tra...

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Bibliographic Details
Published in:Lipids 1998-09, Vol.33 (9), p.861-867
Main Authors: Lie Ken Jie, Marcel S. F., Fu, Xun
Format: Article
Language:English
Subjects:
Alcohols
Esters
Fatty acids
Fatty Alcohols - chemistry
Fatty Alcohols - metabolism
Lipase - chemistry
Lipase - metabolism
Pentanoic Acids - chemistry
Pentanoic Acids - metabolism
Stearic Acids - chemistry
Stearic Acids - metabolism
Structure-Activity Relationship
Substrate Specificity
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Summary:The esterification of five medium‐ and long‐chain acetylenic alcohols (2‐nonyn‐1‐ol, 10‐undecyn‐1‐ol, 6‐octadecyn‐1‐ol, 9‐octadecyn‐1‐ol, and 13‐docosyn‐1‐ol), seven olefinic alcohols (cis‐3‐nonen‐1‐ol, 10‐undecen‐1‐ol, cis‐6‐octadecen‐1‐ol, cis‐9‐octadecen‐1‐ol, trans‐9‐octadecen‐1‐ol, trans‐9, trans‐11‐octadecadien‐1‐ol, cis‐9, cis‐12‐octadecadien‐1‐ol), and four short‐chain unsaturated alcohols (allyl alcohol, 3‐butyn‐1‐ol, 3‐pentyn‐1‐ol, and cis‐2‐penten‐1‐ol) with pentanoic or stearic acid in the presence of various lipase preparations was studied. With the exception of 2‐nonyn‐1‐ol, where Lipase AY‐30 (Candida rugosa) was used as the biocatalyst, the esterification of C11, C18, and C22 acetylenic alcohols with pentanoic acid appeared to be generally unaffected by the presence of an acetylenic bond in the alcohol as relatively high yields of the corresponding esters (78–97%) were obtained. However, medium‐ and long‐chain olefinic alcohols were discriminated by Lipase AY‐30, Lipolase 100T (Rhizomucor miehei), and especially by porcine pancreatic lipase (PPL), when esterification was conducted with pentanoic acid. Esterification of medium‐and long‐chain acetylenic or olefinic alcohols with a long‐chain fatty acid, stearic acid, was very efficient except when Lipase AY‐30 and Lipolase 100T were used. Short‐chain unsaturated alcohols were much more readily discriminated. 3‐Pentyn‐1‐ol and 3‐butyn‐1‐ol were difficult (
ISSN:0024-4201
1558-9307
DOI:10.1007/s11745-998-0282-y