Synthesis of trehalose monomycolate (TMM) analogs for probing the specificity of macrophage-inducible C-type lectin (Mincle)

Date of Publication

2016

Document Type

Master's Thesis

Degree Name

Master of Science in Chemistry

College

College of Science

Department/Unit

Chemistry

Thesis Adviser

Derrick C. Ethelbhert
Gladys C. Completo

Defense Panel Chair

Jaime Raul O. Janairo

Defense Panel Member

Francisco Franco, Jr.
Ruel Nacario

Abstract/Summary

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

Abstract Format

html

Language

English

Format

Electronic

Accession Number

CDTG006770

Shelf Location

Archives, The Learning Commons, 12F Henry Sy Sr. Hall

Physical Description

1 computer optical disc ; 4 3/4 in.

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