(N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)glycine methyl ester | 145520-95-2

• 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-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)glycine methyl ester
• 英文别名: 1-O-β-D-(N-t-butyloxycarbonylserylglycine methyl ester)-galactopyranoside；methyl 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanoyl]amino]acetate
• CAS: 145520-95-2
• 化学式: C₁₇H₃₀N₂O₁₁
• 分子量: 438.432
• InChiKey: LJECYWGVOZLXSF-VGWZMKPKSA-N

物化性质

• 沸点：
  690.2±55.0 °C(predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  193
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)glycine methyl ester 以 水 为溶剂， 以68%的产率得到1-O-β-D-(N-t-butoxycarbonylseryl-glycine)galactopyranoside
  参考文献：
  名称：

  Enzymatic synthesis of β-galactosyldipeptides and of β-1,3-digalactosylserine derivatives using β-galactosidase

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)85615-5
• 作为产物：
  描述：

  methyl 2-(2-((t-butoxycarbonyl)amino)-3-hydroxypropanamido)-acetate 、 尾-D-Galactoside,2-nitrophenyl(9CI) 以14%的产率得到(N-tert-butoxycarbonyl-3-O-β-D-galactopyranosyl-L-seryl)glycine 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 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.
• 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.