Organic Letters
Organic Letters
5 years ago

Synthesis of a Glycosylphosphatidylinositol Anchor Derived from Leishmania donovani That Can Be Functionalized by Cu-Catalyzed Azide–Alkyne Cycloadditions

Synthesis of a Glycosylphosphatidylinositol Anchor Derived from Leishmania donovani That Can Be Functionalized by Cu-Catalyzed Azide–Alkyne Cycloadditions
Geert-Jan Boons, Xiuru Li, Zoeisha S. Chinoy, Ning Ding
A flexible assembly strategy has been developed for the synthesis of Leishmania donovani GPI anchors that bear a clickable alkyne tag. This strategy is based on the use of the 2-naphthylmethyl (Nap) ethers and levulinoyl (Lev) ester for permanent protection of hydroxyls. Removal of seven Nap ethers by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone made it possible to prepare GPIs having an alkyne functionality that could be modified by Cu(I)-catalyzed [3 + 2] cycloadditions to install tags for imaging studies.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01703

DOI: 10.1021/acs.orglett.7b01703

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