Biomedical subjects

Clay S Bennett

Publications and source records attributed to Clay S Bennett.

4 recordsLinked to original sources

PubMed2006

Sugar-assisted ligation of N-linked glycopeptides with broad sequence tolerance at the ligation junction.

A novel method for the synthesis of N-linked glycopeptides using the sugar-assisted ligation strategy from cysteine free peptides is presented. The ligation junction tolerates a variety of amino acids, favoring less hindered amino acids and those with side chains that could serve as a general base in the ligation pathway. Since our approach allows the ligation of difficult junctions, the method could be applied to the synthesis of large peptides by enzymatic removal of the sugar moiety. Alternatively, more complex glycopeptides can be synthesized using glycosyltransferases. Together, this sequence of reactions should be amenable to the synthesis of glycopeptides and glycoproteins and their deglycosylated products.

Carbohydrates↗

PubMed2005

Advances in glycoprotein synthesis.

The development of chemical and enzymatic methods for the synthesis of homogeneous glycoproteins is a fascinating challenge at the interface between chemistry and biology. Discussed here are the currently available methods for preparation of homogeneous glycoproteins. These methods include (1) glycopeptide ligation; (2) glycoprotein remodeling; and (3) in vivo suppressor tRNA technology.

Carbohydrate Conformation↗

PubMed2003

Total synthesis of (+)-spongistatin 1. An effective second-generation construction of an advanced EF Wittig salt, fragment union, and final elaboration.

A stereocontrolled, total synthesis of (+)-spongistatin 1 (1) has been achieved. Union of a second-generation EF Wittig salt (+)-3 with the advanced ABCD aldehyde (-)-4, followed by regioselective macrolactonization and global deprotection afforded (+)-spongistatin 1 (1). The longest linear sequence, 29 steps, proceeded in 0.5% overall yield.

Aldehydes↗

PubMed2002

Spongistatin synthetic studies. An efficient, second-generation construction of an advanced ABCD intermediate.

[reaction: see text] A short, efficient, and stereocontrolled synthesis of (-)-4, an advanced ABCD subunit of the spongistatins, has been achieved. Central to the synthetic strategy is the multicomponent linchpin union of silyl dithianes with epoxides to access both the AB and CD fragments. Fragment coupling was then achieved via an efficient stereoselective aldol reaction. The linear sequence required 22 steps and proceeded in 4.0% overall yield.

Animals↗