c[L-aspartyl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonyl] | 1426832-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: c[L-aspartyl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonyl]
• 英文别名: 2-[(2S,5S)-5-[(1R)-1-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]-3,6-dioxopiperazin-2-yl]acetic acid
• CAS: 1426832-53-2
• 化学式: C₁₆H₂₅N₃O₁₀
• 分子量: 419.389
• InChiKey: WVTSDVWLEHGRAU-NDQIWNFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  204
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl chloride 在 哌啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium methylate 、 1-羟基苯并三唑 、 copper(II) sulfate 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 mercury dibromide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 c[L-aspartyl-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonyl]
  参考文献：
  名称：

  α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

  摘要：

  This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(alpha GalNAc)Ser] 3 and cyclo[Asp-(alpha GalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids alpha GalNAc-Ser 7 or alpha GalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by a-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with alpha GalN(3)Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 mu M), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.027

文献信息

• α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi
  作者：Maristela B. Martins-Teixeira、Vanessa L. Campo、Monica Biondo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Ivone Carvalho

  DOI：10.1016/j.bmc.2013.01.027

  日期：2013.4

  This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(alpha GalNAc)Ser] 3 and cyclo[Asp-(alpha GalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids alpha GalNAc-Ser 7 or alpha GalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by a-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with alpha GalN(3)Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 mu M), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%). (C) 2013 Elsevier Ltd. All rights reserved.