Globo synthesis

SOLID-PHASE SYNTHESIS OF THE HEXASACCHARIDE GLOBO-H ANTIGEN PROGRESS AND LIMITATIONS... 

Scheme 2.18 Solid-phase synthesis of the globo-H trisaccharide antigen.

SCHEME 3.28 Programmable one-pot synthesis of Globo-H. CIBn, o-chlorobcnz.yl NBz,... 

SCHEME 12.8 Danishefsky s first-generation total synthesis of Globo-H ceramide. DMDO, dimethyldioxirane TIPS, triisopropylsilyl. 

SCHEME 12.9 Danishefsky s second-generation synthesis of Globo-H. DMF, /V,/V-dimcth-ylformamide DTBP, 2,6-di-tert-butylpyridine IDCP, iodonium di-.vym-collidinc perchlorate LHMDS, lithium bis(trimethylsilyl)amide. 

Yet another efficient assembly of Globo-H glycan was reported by Huang and coworkers [89] via a multicomponent one-pot synthesis. Their approach relies on preactivation-based iterative glycosylation of thiotolyl donors using TolSCl/AgOTf... 

SCHEME 12.13 Seeberger s automated synthesis of Gb3 and Globo-H. TCA, trichloro acetyl. 

Kojima Y, Fukumoto S, Fumkawa K, Okajima T, Wiels J, Yokoyama K, Suzuki Y, Urano T, Ohta M, Fumkawa K. Molecular cloning of globotriaosylceramide/CD77 synthase, a glycosyl-transferase that initiates the synthesis of globo series glycosph-ingolipids. J. Biol. Chem. 2000 275 15152-15156. 

JU. Cloning of Gbs synthase, the key enzyme in globo-series 55. glycosphingolipid synthesis, predicts a family of 1,4 glycosyn-transferases conserved in plants, insects and mammals. J. Biol. 56. Chem. 2000 275 25315-25321. 

---