Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

TY - JOUR

T1 - Combining Click Reactions for the One-Pot Synthesis of Modular Biomolecule Mimetics

AU - Brinko, Anne

AU - Risinger, Christian

AU - Lambert, Annie

AU - Blixt, Ola

AU - Grandjean, Cyrille

AU - Jensen, Henrik H.

PY - 2019/9/20

Y1 - 2019/9/20

N2 - Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

AB - Here, we report on the first combined one-pot use of the two so-called "click reactions": The thiol-ene coupling and the copper-catalyzed alkyne-azide cycloaddition. These reactions were employed in an alternating and one-pot fashion to combine appropriately functionalized monomeric carbohydrate building blocks to create mimics of trisaccharides and tetrasaccharides as single anomers, with only minimal purification necessary. The deprotected oligosaccharide mimics were found to bind both plant lectins and human galectin-3.

U2 - 10.1021/acs.orglett.9b02811

DO - 10.1021/acs.orglett.9b02811

M3 - Letter

C2 - 31502847

SN - 1523-7060

VL - 21

SP - 7544

EP - 7548

JO - Organic Letters

JF - Organic Letters

IS - 18

ER -