845532-32-3Relevant academic research and scientific papers
Fidelity and Promiscuity of a Mycobacterial Glycosyltransferase
Yamatsugu, Kenzo,Splain, Rebecca A.,Kiessling, Laura L.
, p. 9205 - 9211 (2016/08/05)
Members of the genus Mycobacterium cause devastating human diseases, including tuberculosis. Mycobacterium tuberculosis can resist some antibiotics because of its durable and impermeable cell envelope. This barrier is assembled from saccharide building bl
The Use of Pyranoside-into-Furanoside Rearrangement and Controlled O(5) → O(6) Benzoyl Migration as the Basis of a Synthetic Strategy to Assemble (1→5)- and (1→6)-Linked Galactofuranosyl Chains
Argunov, Dmitry A.,Krylov, Vadim B.,Nifantiev, Nikolay E.
supporting information, p. 5504 - 5507 (2016/11/17)
A new pyranoside-into-furanoside (PIF) rearrangement of selectively protected galactopyranosides, followed by controlled O(5) → O(6) benzoate migration, gives either 5-OH or 6-OH products. It has been applied for the synthesis of four oligosaccharides related to the galactomannan from Aspergillus fumigatus. The assembly of target oligosaccharides containing both (1→5) and (1→6) linkages between galactofuranosyl residues was performed by applying terminal mannoside and digalactofuranoside blocks, forming a versatile approach toward fungal and bacterial carbohydrate antigens containing both 5-O- and 6-O-substituted galactofuranoside residues.
Synthesis of galactofuranose-based acceptor substrates for the study of the carbohydrate polymerase GlfT2
Splain, Rebecca A.,Kiessling, Laura L.
scheme or table, p. 3753 - 3759 (2010/08/03)
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 β-(1,5) and β-(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.
An efficient and concise synthesis of a β-(1→6)-linked d-galactofuranosyl hexasaccharide
Zhang, Guohua,Fu, Mingkun,Ning, Jun
, p. 155 - 159 (2007/10/03)
A β-(1→6)-linked d-galactofuranosyl hexasaccharide was synthesized efficiently in a block construction manner by the well-known Schmidt glycosylation method using 6-O-acetyl-2,3,5-tri-O-benzoyl-β-d- galactofuranosyl trichloroacetimidate (1) and allyl 2,3,
