Ríos Pablo, Mooibroek Tiddo J, Carter Tom S, Williams Christopher, Wilson Miriam R, Crump Matthew P, Davis Anthony P
School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email:
Chem Sci. 2017 May 1;8(5):4056-4061. doi: 10.1039/c6sc05399h. Epub 2017 Mar 30.
Carbohydrate receptors with a chiral framework have been generated by combining a tetra-aminopyrene and a -symmetrical triamine isophthalamide spacers bearing water-solubilising groups. These "synthetic lectins" are the first to show enantiodiscrimination in aqueous solution, binding -acetylglucosamine (GlcNAc) with 16 : 1 enantioselectivity. They also show exceptional affinities. GlcNAc is bound with up to 1280 M, more than twice that measured for previous synthetic lectins, and three times the value for wheat germ agglutinin, the lectin traditionally employed to bind GlcNAc in glycobiological research. Glucose is bound with = 250 M, again higher than previous synthetic lectins. The results suggest that chirality can improve complementarity to carbohydrate substrates and may thus be advantageous in synthetic lectin design.
通过将四氨基芘和带有水溶性基团的对称三胺间苯二甲酰胺间隔基相结合，生成了具有手性框架的碳水化合物受体。这些“合成凝集素”是首个在水溶液中表现出对映体识别能力的，以16:1的对映选择性结合β-乙酰氨基葡萄糖（GlcNAc）。它们还表现出非凡的亲和力。GlcNAc与之结合的亲和力高达1280 M，是之前合成凝集素测量值的两倍多，是糖生物学研究中传统用于结合GlcNAc的麦胚凝集素数值 的三倍之多。葡萄糖与之结合亲和力为Kd = 2５0 M，同样高于之前的合成凝集素。结果表明，手性可以改善与碳水化合物底物的互补性，因此在合成凝集素设计中可能具有优势。
