Synthetic studies towards Mannopeptamycins: De novo synthesis of tyrosine, serine and threonine disaccharides

ORGN 179

Satheesh Babu Ravula, satheeshbabur@hotmail.com, Sanjeeva R Guppi, sanjeev_ssk@yahoo.com, and George A. O'Doherty, george.odoherty@mail.wvu.edu. C. Eugene Bennett Department of Chemistry, West Virginia University, 284 Prospect Street, 217 Clark Hall of Chemistry, WVU, Morgantown, WV 26506
Mannopeptimicins are cyclic hexa-peptides with a disaccharide side chain, which possesses potent antibacterial activity against gram-positive bacteria with good activity against drug resistant (MDR) bacteria. The disaccharide fragment of Mannopeptimicin is known to be the key to activity. Recently we have synthesized a disaccharide fragment in 6 steps from tyrosine in 44% overall yield using our de novo approach to carbohydrates. Similarly, unnatural sugar analogues of tyrosine, serine and threonine disaccharides were also synthesized. These results will be presented along with further utilization of our de novo approach towards the synthesis of pyrano-nucleoside analogues.