Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 18, Issue 11, Pages 3753-3759Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.04.068
Keywords
Galactan; Carbohydrate polymer; Glycosyl acceptor; Galactofuranose; Glycosyltransferase; Cross-metathesis; Mycobacterium tuberculosis
Funding
- Tetrahedron
- National Institutes of Health [AI063596]
- American Chemical Society Division of Medicinal Chemistry
- NIH [NIH NCRR 1S10RR024601-01]
- NSF [NSF CHE-9974839, CHE-9208463]
- NATIONAL CENTER FOR RESEARCH RESOURCES [S10RR024601] Funding Source: NIH RePORTER
- NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES [R01AI063596, R56AI063596] Funding Source: NIH RePORTER
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Despite the prevalence and importance of carbohydrate polymers, the molecular details of their biosynthesis remain elusive. Many enzymes responsible for the synthesis of carbohydrate polymers require a 'primer' or 'initiator' carbohydrate sequence. One example of such an enzyme is the mycobacterial galactofuranosyltransferase GlfT2 (Rv3808c), which generates an essential cell wall building block. We recently demonstrated that recombinant GlfT2 is capable of producing a polymer composed of alternating beta-(1,5) and beta-(1,6)-linked galactofuranose (Galf) residues. Intriguingly, the length of the polymers produced from a synthetic glycosyl acceptor is consistent with those found in the cell wall. To probe the mechanism by which polymer length is controlled, a collection of initiator substrates has been assembled. The central feature of the synthetic route is a ruthenium-catalyzed cross-metathesis as the penultimate transformation. Access to synthetic substrates has led us to postulate a new mechanism for length control in this template-independent polymerization. Moreover, our investigations indicate that lipids possessing but a single galactofuranose residue can act as substrates for GlfT2. (C) 2010 Elsevier Ltd. All rights reserved.
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