Synthesis of Mannosyl and Oligomannosyl Threonine Building Blocks found on the Mycobacterium tuberculosis 45 kDa MPT 32 Glycoprotein

Abstract

Mycobacterium tuberculosis secretes a 45 kDa glycoprotein (MPT 32) carrying mannosylated threonine residues. A general strategy was developed to couple peracetylated mannose, α -(1,2)-linked mannobiose or mannotriose to Fmoc-threonine-benzyl ester. Activation of mannosyl acetates or fluorides by borontrifluoride etherate gave the desired Fmoc-glycosyl amino acid building blocks in good yields. The synthesis leads to stable compounds and can easily be scaled up.