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Monatin, Its Stereoisomers and Derivatives: Modeling the Sweet Taste Chemoreception Mechanism
Author(s) -
Bassoli Angela,
Borgonovo Gigliola,
Busnelli Gilberto,
Morini Gabriella,
Merlini Lucio
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400916
Subject(s) - chemistry , intramolecular force , stereocenter , stereochemistry , hydrogen bond , ring (chemistry) , taste , sweet taste , molecule , enantioselective synthesis , organic chemistry , food science , catalysis
The sweet natural compound monatin 1 has two stereogenic centers, and the 2 S ,4 S absolute configuration has been attributed previously to the natural isomer. Among the four stereoisomers of monatin, three of them, particularly the 2 R ,4 R isomer, tastes intensely sweet. The conformations of the four compounds have been studied by means of molecular modelling techniques. Both the diastereoisomeric forms show strong intramolecular hydrogen bonds which involve different functional groups and give rise to two different minimum energy conformations. The tertiary alcohol group in monatin seems to be indirectly involved in the generation of the taste, acting as an important contraint in generating the active conformation. The most important glucophores have been identified in the terminal –NH 3 + and –COO – groups and in the indole ring by comparison with known topological models of sweet compounds and through the synthesis of appropriate derivatives in which some of these groups are lacking or modified. The relative affinity of each stereoisomer for its putative sweet taste receptor has been estimated semiquantitatively with the pseudoreceptor modelling technique. The predicted activity calculated with this technique is in good agreement with the experimental data and explains why the 2 R ,4 R isomer (and not the natural 2 S ,4 S isomer) is the sweetest of the series. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)