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Chemoenzymatic synthesis and lectin recognition of a selectively fluorinated glycoprotein.

Abstract：

:A chemoenzymatic glycosylation remodeling method for the synthesis of selectively fluorinated glycoproteins is described. The method consists of chemical synthesis of a fluoroglycan oxazoline and its use as donor substrate for endoglycosidase (ENGase)-catalyzed transglycosylation to a GlcNAc-protein to form a homogeneous fluoroglycoprotein. The approach was exemplified by the synthesis of fluorinated glycoforms of ribonuclease B (RNase B). An interesting finding was that fluorination at the C-6 of the 6-branched mannose moiety in the Man3GlcNAc core resulted in significantly enhanced reactivity of the substrate in enzymatic transglycosylation. A structural analysis suggests that the enhancement in reactivity may come from favorable hydrophobic interactions between the fluorine and a tyrosine residue in the catalytic site of the enzyme (Endo-A). SPR analysis of the binding of the fluorinated glycoproteins with lectin concanavalin A (con A) revealed the importance of the 6-hydroxyl group on the α-1,6-branched mannose moiety in con A recognition. The present study establishes a facile method for preparation of selectively fluorinated glycoproteins that can serve as valuable probes for elucidating specific carbohydrate-protein interactions.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Orwenyo J,Huang W,Wang LX

doi

10.1016/j.bmc.2013.03.009

subject

Has Abstract

pub_date

2013-08-15 00:00:00

pages

4768-77

issue

16

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00212-5

journal_volume

21

pub_type

杂志文章

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