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d-Glucose based syntheses of β-hydroxy derivatives of l-glutamic acid, l-glutamine, l-proline and a dihydroxy pyrrolidine alkaloid

机译:L-谷氨酸,L-谷氨酰胺,L-脯氨酸和二羟基吡咯烷生物碱的β-羟基衍生物的D-葡萄糖基合成

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The β-hydroxy derivatives of L -glutamic acid, L -glutamine and L -proline, useful for peptide/protein studies, were synthesized starting from D -glucose. The C2 carbon in D -glucose provided the carboxylic acid functionality, while the amino and β-hydroxy groups of the amino acids were amenable from the C3 and C4 hydroxy groups of the sugar, respectively. The key intermediate with appropriate carbon framework of the target molecules was constructed by homologation of a suitable azido- D -glucofuranose derivative using the Arndt–Eistert reaction.
机译:从D葡萄糖开始合成L-乙醇,L-谷氨酰胺和L-脯氨酸,可用于肽/蛋白质研究的β-羟基衍生物。 D-葡糖中的C2碳提供羧酸官能团,而氨基酸的氨基和β-羟基分别可从C3和C4羟基的糖的C3和C4羟基。通过使用ArnDT-ESTERT反应的合适的αzido-dglucofuranose衍生物的同源构建靶分子的关键中间体。

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