Formula: C15H28O2In 2020, Tahiri, Nabil;Fodran, Peter;Jayaraman, Dhineshkumar;Buter, Jeffrey;Witte, Martin D.;Ocampo, Tonatiuh A.;Moody, D. Branch;Van Rhijn, Ildiko;Minnaard, Adriaan J. published 《Total Synthesis of a Mycolic Acid from Mycobacterium tuberculosis》. 《Angewandte Chemie, International Edition》published the findings. The article contains the following contents:
In Mycobacterium tuberculosis, mycolic acids and their glycerol, glucose, and trehalose esters (“cord factor”) form the main part of the mycomembrane. Despite their first isolation almost a century ago, full stereochem. evaluation is lacking, as is a scalable synthesis required for accurate immunol., including vaccination, studies. Herein, we report an efficient, convergent, gram-scale synthesis of four stereo-isomers of a mycolic acid and its glucose ester. Binding to the antigen presenting protein CD1b and T cell activation studies are used to confirm the antigenicity of the synthetic material. The absolute stereochem. of the syn-methoxy Me moiety in natural material is evaluated by comparing its optical rotation with that of synthetic material. To complete the study, the researchers used Oxacyclohexadecan-2-one (cas: 106-02-5) .
Oxacyclohexadecan-2-one(cas:106-02-5) is a natural product found in Lonicera japonica and Angelica archangelica.Formula: C15H28O2 It is a macrocyclic lactone that can be used as a flavoring agent and fragrance ingredient due to its musk flavor/odor.
Reference:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics