862583-35-5Relevant academic research and scientific papers
Monatin, its stereoisomers and derivatives: Modeling the sweet taste chemoreception mechanism
Bassoli, Angela,Borgonovo, Gigliola,Busnelli, Gilberto,Morini, Gabriella,Merlini, Lucio
, p. 2518 - 2525 (2007/10/03)
The sweet natural compound monatin 1 has two stereogenic centers, and the 2S,4S absolute configuration has been attributed previously to the natural isomer. Among the four stereoisomers of monatin, three of them, particularly the 2R,4R 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 -NH3+ 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 semi-quantitatively with the pseudoreceptor modelling technique. The predicted activity calculated with this technique is in good agreement with the experimental data and explains why the 2R,4R isomer (and not the natural 2S,4S isomer) is the sweetest of the series. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
Total synthesis and stereochemistry of cytoblastin
Moreno, Ofir A.,Kishi, Yoshito
, p. 1243 - 1254 (2007/10/03)
The first total synthesis and stereochemical assignment of cytoblastin were reported. Key steps included the palladium-mediated coupling of N-SEM-7-bromoindolactam V ((-)-11) with allylstannane c-13, and osmium tetroxide-mediated dihydroxylation of 14, both of which were stereoselective. The stereochemistry of cytoblastin was determined as 1A via spectroscopic analysis of the pentacyclic derivative 21 of cytoblastin. A connection was then made between the stereochemistry so elucidated and the Kishi/Rando hypothesis for the structural correlation between (S)-1,2-diacylglycerol and tumor promoters for the process of protein kinase C activation. Copyright (C) 1998 Elsevier Science Ltd.
