Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Reexamination Certificate
2006-03-28
2006-03-28
Wilson, James O. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
C536S123100, C536S018500, C536S018600, C536S118000, C536S017400, C536S017500, C536S017900, C536S004100, C536S126000, C514S053000, C435S097000, C435S074000, C435S075000
Reexamination Certificate
active
07019131
ABSTRACT:
The reactivity of a number of p-methylphenyl thioglycoside (STol) donors which are either fully protected or have one hydroxyl group exposed has been quantitatively determined by HPLC in conjunction with the development of a broadly applicable approach for a facile one-pot synthesis of oligosaccharides. The influence on reactivity of the structural effects of different monosaccharide cores and different protecting groups on each glycoside donor is characterized and quantified. In addition, a correlation between glycosyl donor reactivity and the chemical shift of the anomeric proton by 1 H NMR has been established. A database of thioglycosides as glycosyl donors has been created using this reactivity data. The utility is demonstrated by the easy and rapid one-pot assembly of various linear and branched oligosaccharide structures. In addition, a computer program as been described for use as a database search tool and guide for the selection of building blocks for the one-pot assembly of a desired oligosaccharide or a library of individual oligosaccharides.
REFERENCES:
patent: 6323339 (2001-11-01), Seeberger et al.
Hanessian, S., “Preparative Carbohydrate Chemistry”, 1997, Marcel Dekker, Inc. (New York-Basel-Hong Kong), pp. 313-338.
Takahashi, et al., “Synthetic Study of Oligosaccharide Library Toward Automation-Combinatorial Synthesis and Structure-Activity Relationship of Oligosaccharides having Phytoalexin Elicitor Activity”,Tennen Yuki Kagobutsu Toronkai Koen Yoshishu2000, 42, 121-126.
Baasov Timor
Ollmann Ian
Wong Chi-Huey
Ye Xin-Shan
Zhang Zhiyuan
Khare Devesh
Lewis Donald G.
The Scripps Research Institute
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