Total Synthesis and Proof of Structure of a Human Breast Tumor (Globo-H) Antigen

Autor:	Shuanghua Hu, Samuel J. Danishefsky, In Jong Kim, Ohyun Kwon,†,‡ and, John T. Randolph, Tae Kyo Park, Mark T. Bilodeau
Rok vydání:	1996
Předmět:	Stereochemistry Total synthesis General Chemistry H antigen Ring (chemistry) Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Antigen Galactose Human breast Derivative (chemistry)
Zdroj:	Journal of the American Chemical Society. 118:11488-11500
ISSN:	1520-5126 0002-7863
Popis:	The 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.)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::24faddf98e369df7eb88ca19e6f447ad https://doi.org/10.1021/ja962048b Zobrazit plný text záznamu