N-allyloxycarbonyl-3-O-(6-O-β-D-galactopyranosyl-β-D-galactopyranosyl)-L-serine methyl ester | 145521-07-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-allyloxycarbonyl-3-O-(6-O-β-D-galactopyranosyl-β-D-galactopyranosyl)-L-serine methyl ester
• 英文别名: 6-O-β-D-galactopyranosyl-1-O-β-D-(N-allyloxycarbonylserine methyl ester)-galactopyranoside；methyl (2S)-2-(prop-2-enoxycarbonylamino)-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropanoate
• CAS: 145521-07-9
• 化学式: C₂₀H₃₃NO₁₅
• 分子量: 527.48
• InChiKey: YBHHWBQFVXQQLQ-GRTKDTLMSA-N

物化性质

• 沸点：
  819.6±65.0 °C(predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  243
• 氢给体数：
  8
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1-O-β-D-(N-allyloxycarbonyl-L-serine methyl ester)-galactopyranoside 、 尾-D-Galactoside,2-nitrophenyl(9CI) 反应 3.0h， 以3%的产率得到N-allyloxycarbonyl-3-O-(6-O-β-D-galactopyranosyl-β-D-galactopyranosyl)-L-serine methyl ester
  参考文献：
  名称：

  Enzymatic synthesis of some O-β-d-digalactosyl glycopeptides, using β-d-galactosidase

  摘要：

  Disaccharide-peptide conjugates were obtained in yields of 30-50% from o-nitrophenyl beta-D-galactopyranoside by employing beta-D-galactosidase from E. coli as catalyst. Two series of beta-D-galactosyldipeptides were examined as galactosyl acceptors. They both contain an L-serine residue beta-linked to the anomeric carbon of galactose. In the first series, serine is in the N-terminal position of the dipeptide; in the second series, serine is in the C-terminal position. The second amino acid is L-alanine or glycine. Some of our substrates gave a high yield of beta(1 --> 3)-digalactosyldipeptide derivatives and all gave very little of the beta-(1 --> 6) regioisomer. The conditions and the limitations of the transgalactosylation reaction are discussed.

  DOI：

  10.1016/0008-6215(93)84137-u

文献信息

• Enzymatic synthesis of β-galactosyldipeptides and of β-1,3-digalactosylserine derivatives using β-galactosidase
  作者：Sandra Attal、Sylvie Bay、Danièle Cantacuzene

  DOI：10.1016/s0040-4020(01)85615-5

  日期：1992.1

  The transgalactosidation from lactose to dipeptides has been achieved using beta-galactosidase from E. Coli as catalyst. Two series of dipeptides have been studied, each of them containing a serine residue. The best condensations occur when serine is at the N-terminal end of the dipeptide. Mild hydrolysis of the ester group of the labile glycosyl-dipeptide derivatives has been achieved using subtilisin. We also describe the condensation of lactose with beta-galactosyl serine to give beta-1,3-digalactosyl-serine derivatives.
• Enzymatic synthesis of some O-β-d-digalactosyl glycopeptides, using β-d-galactosidase
  作者：Sylvie Bay、Abdelkader Namane、Danièle Cantacuzene

  DOI：10.1016/0008-6215(93)84137-u

  日期：1993.10

  Disaccharide-peptide conjugates were obtained in yields of 30-50% from o-nitrophenyl beta-D-galactopyranoside by employing beta-D-galactosidase from E. coli as catalyst. Two series of beta-D-galactosyldipeptides were examined as galactosyl acceptors. They both contain an L-serine residue beta-linked to the anomeric carbon of galactose. In the first series, serine is in the N-terminal position of the dipeptide; in the second series, serine is in the C-terminal position. The second amino acid is L-alanine or glycine. Some of our substrates gave a high yield of beta(1 --> 3)-digalactosyldipeptide derivatives and all gave very little of the beta-(1 --> 6) regioisomer. The conditions and the limitations of the transgalactosylation reaction are discussed.