(N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)-L-alanine methyl ester | 145520-97-4

• 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-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)-L-alanine methyl ester
• CAS: 145520-97-4
• 化学式: C₁₈H₃₂N₂O₁₁
• 分子量: 452.459
• InChiKey: NELSZYWXZVGTQN-XYZZWKNVSA-N

物化性质

• 沸点：
  689.2±55.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.63
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  193.11
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)-L-alanine methyl ester 、 尾-D-Galactoside,2-nitrophenyl(9CI) 反应 3.0h， 以29%的产率得到-L-alanine 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
• 作为产物：
  描述：

  Boc-Ser-Ala-OMe 、 尾-D-Galactoside,2-nitrophenyl(9CI) 以11%的产率得到(N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)-L-alanine 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.