As a part of our study of microbial cutinases, a mixture of oligomers
of 16-hydroxyhexadecanoic acid has been prepared by partial polymeriza
tion to serve as defined substrates. The mixture has been characterize
d by spectroscopic and chromatographic methods. Enzyme-catalyzed hydro
lysis of the oligomers using fungal lipase, fungal cutinase or bacteri
al lipase required the addition of beta-cyclodextrin to the reaction m
edium, whereas apple and other naturally occurring cutins can be enzym
atically hydrolyzed without the aid of this cyclic oligosaccharide. Th
e difference in reactivity may be due to the greater hydrophobicity of
the synthetic oligomers compared with natural cutin polymers.