The Influence of Selected O-alkyl Derivatives of Cyclodextrins on the Enzymatic Decomposition of L-tryptophan by L-tryptophan Indole-Lyase

Tomasz Gubica, Elzbieta Winnicka, Andrzej Temeriusz, Marianna Kańska

Carbohydr Res. 2009 Feb 17;344(3):304-10.

PMID: 19084828

Abstract:

A series of O-alkyl derivatives of cyclodextrin: heksakis[2,3,6-tri-O-(2'-methoxyethyl)]-alpha-cyclodextrin; heksakis(2,3-di-O-methyl)-alpha-cyclodextrin; heptakis(2,3-di-O-methyl)-beta-cyclodextrin; heksakis[2,3-di-O-methyl-6-O-(2'-methoxyethyl)]-alpha-cyclodextrin; heptakis[2,3-di-O-methyl-6-O-(2'-methoxyethyl)]-beta-cyclodextrin; heksakis[2,3-di-O-(2'-methoxyethyl)]-alpha-cyclodextrin and heptakis[2,3-di-O-(2'-methoxyethyl)]-beta-cyclodextrin have been synthesized. Purity and composition of the obtained substances were examined. The cyclodextrin derivatives listed above as well as (2-hydroxypropyl)-alpha-cyclodextrin and (2-hydroxypropyl)-beta-cyclodextrin, the two commercially available ones, have been investigated as the additives in the course of enzymatic decomposition of L-tryptophan by L-tryptophan indole-lyase. It has been found that each of cyclodextrin derivatives causes the inhibition of enzymatic process, both competitive and non-competitive. The competitive inhibition is connected with the formation of inclusion complexes between cyclodextrins and L-tryptophan, related to the geometry of these complexes. The mechanism of the non-competitive inhibition is not so evident; it could be related to the formation of the cyclodextrin complexes on the surface of the enzyme, leading to the change in the flexibility of the enzyme molecule.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP128446333	(2-Hydroxypropyl)-α-cyclodextrin		128446-33-3	Price