Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen
journal contribution
posted on 1996-11-20, 00:00 authored by Tae Kyo Park, In Jong Kim, Shuanghua Hu, Mark T. Bilodeau, John T. Randolph, Ohyun Kwon, Samuel J. DanishefskyThe total synthesis of the Hakomori MBr1 antigen, heavily
expressed on human breast tumors, is related.
The construction involved the assembly of four glycals:
(17 (twice), 18, 20, and
26) and an l-fucose derivative,
34.
The sensitivity of the stereochemistry of sulfonamido
galactosylation by a terminal galactose ring as a function
of
the state of protection status of its C4 alcohol was
exploited in a key step. (See the formation of compound
51.)
The synthesis served to confirm the Hakomori assignment of
structure, and paves the way for immunoconjugation.
(See compound 64.)
