Synthesis of trehalose monomycolate (TMM) analogs for the specificity of C-type lectin (Mincle)
Date of Publication
Master of Science in Chemistry
College of Science
Derrick C. Ethelbhert
Gladys C. Completo
Defense Panel Chair
Jaime Raul O. Janairo
Defense Panel Member
Francisco Franco, Jr.
The macrophage-inducible C-type lectin (Mincle) is a protein involved in the recognition of trehalose monomycolate (TMM) and trehalose dimycolate (TDM), glycolipids produced by mycobacteria, including the human pathogen Mycobacterium tuberculosis. This project aimed to establish a chemical synthesis of TMM analogs that will be used to probe the molecular details of this carbohydrate protein interactions. The three (3) TMM analogs were synthesized using the designed general synthetic procedure for trehalose monoesters with 2,3- antistereochemistry. Incorporation of the desired functional groups to form mycolates was achieved by enolate alkylation, followed by Noyoris asymmetric reduction of b,b- ketoesters then antiselective alkylation according to Frater to give b,b- hydroxy alcohols as the key steps. Regioselective debenzylation of trehalose unit using DIBAL-H was used to improve monoester formation. Thus, we prepared analogs 41A, 41B and 41C in moderate to high yields. In addition to serving as useful biochemical tools, these molecules may have potential as novel adjuvants
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Sangalang, R. (2016). Synthesis of trehalose monomycolate (TMM) analogs for the specificity of C-type lectin (Mincle). Retrieved from https://animorepository.dlsu.edu.ph/etd_masteral/5159