N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester | 237753-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester
• 英文别名: tert-butyl 2-methyl-2-[[2-methyl-2-[[(2S,3R)-2-(phenylmethoxycarbonylamino)-3-[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxybutanoyl]amino]propanoyl]amino]propanoate
• CAS: 237753-46-7
• 化学式: C₃₈H₅₅N₃O₁₆
• 分子量: 809.865
• InChiKey: YSEFWJRPMOMNPE-RLLNJBQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  57
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  247
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester 在 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyryl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester
  参考文献：
  名称：

  Influence of glycosylation on the conformational preferences of folded oligopeptides

  摘要：

  Synthesis, characterization, and conformational analysis by FT-IR absorption, H-1 NMR and X-ray diffraction techniques are described for a series of side-chain O-glycosylated Thr peptides of different main-chain length rich in the helicogenic Aib residue. The results obtained, compared with those of related peptides containing side-chain protected Thr and Ser residues and host Aib homo-oligomers, also reported in this work, provided new information on the preferred conformation of the naturally occurring antifreeze glycopeptides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00098-9
• 作为产物：
  描述：

  H-Aib-Aib-O(t-Bu) 、 在 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以57%的产率得到N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-threonyl-α-aminoisobutyryl-α-aminoisobutyric acid tert-butyl ester
  参考文献：
  名称：

  Influence of glycosylation on the conformational preferences of folded oligopeptides

  摘要：

  Synthesis, characterization, and conformational analysis by FT-IR absorption, H-1 NMR and X-ray diffraction techniques are described for a series of side-chain O-glycosylated Thr peptides of different main-chain length rich in the helicogenic Aib residue. The results obtained, compared with those of related peptides containing side-chain protected Thr and Ser residues and host Aib homo-oligomers, also reported in this work, provided new information on the preferred conformation of the naturally occurring antifreeze glycopeptides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00098-9