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首页> 外文期刊>Chemistry: A European journal >A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizesb-Mannose and b-Mannosides
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A Chiral Pyrrolic Tripodal Receptor Enantioselectively Recognizesb-Mannose and b-Mannosides

机译：手性吡咯三脚架受体对映选择性识别b-甘露糖和b-甘露糖苷。

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摘要

Biomimetic receptors for carbohydrates have been widelyused to investigate the recognition phenomena occurring in biological systems.[1] Among the plethora of synthetic receptors for carbohydrates reported in the literature, only a limited number are chiral. In addition, of the several papers dealing with recognition of carbohydrates by chiral synthetic receptors,[2–20] only a few are concerned with the effect of receptor s chirality on the enantioselective recognition of sugars.[2–8] This is somewhat surprising because selective recognition can be expected when enantiomerically pure natural saccharides bind to opposite enantiomers of a chiral receptor. Indeed, apart from the extensive work of Diederich and co-workers on dendritic clefts and cyclophanic and macropolycyclic receptors,[2] following the first report by Davis and co-workers,[3] very few investigations were specifically focused on the enantioselective recognition of monosaccharides by chiral receptors.[4–8] In particular, to our knowledge, the enantioselective recognition of mannosides has only been reported in two cases, in which 1-octyl-a-d-mannopyranoside binds to the enantiomers of the receptor with little or no discrimination.[2b, 6] We have recently reported a family of pyrrolic tripodal receptors possessing distinguished recognition properties towards monosaccharides.[21] We describe herein the first member of a new generation of chiral tripodal receptors, showing unprecedented affinities towards mannosides even in polar solvents, and marked selectivities with respect to other monosaccharides; most remarkably, the all-S enantiomer of the receptor selectively binds to b-mannose and b-mannosides with an outstanding enantiomeric discrimination with respect to the all-R enantiomer, proving that chirality of the receptor is a key feature in the selective recognition of mannose.
机译：碳水化合物的仿生受体已被广泛用于研究生物系统中发生的识别现象。[1]在文献中报道的过多的碳水化合物合成受体中，只有少数是手性的。此外，在有关手性合成受体识别碳水化合物的几篇论文中，[2-20]仅有少数涉及受体的手性对糖的对映选择性识别的影响。[2-8]这有点令人惊讶因为当对映体纯的天然糖与手性受体的相反对映体结合时，可以预期选择性识别。确实，除了Diederich及其同事在树突状裂隙以及环斑和大多环受体[2]上的广泛研究之外，[2]在Davis及其同事的首次报告之后[3]，很少有研究专门针对对映体选择性识别[4-8]特别是，据我们所知，仅在两种情况下才报道了对甘露糖苷的对映选择性识别，其中1-辛基-ad-甘露吡喃糖苷几乎或完全不与受体的对映体结合歧视。[2b，6]我们最近报道了一个对三糖具有独特识别特性的吡咯三脚形受体家族。[21]我们在本文中描述了新一代手性三脚架受体的第一成员，即使在极性溶剂中，对甘露糖苷也显示出前所未有的亲和力，并且对其他单糖具有明显的选择性。最显着的是，该受体的all-S对映体选择性结合b-甘露糖和b-甘露糖苷，对all-R对映体具有出色的对映体鉴别能力，证明该受体的手性是选择性识别B-甘露糖的关键特征。甘露糖。

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