AcNHSer(OBn)Ser(OBn)SerAlaCONH2 | 849063-77-0

• 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: AcNHSer(OBn)Ser(OBn)SerAlaCONH2
• 英文别名: Ac-Ser(Bn)-Ser(Bn)-Ser-Ala-NH2；(2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-phenylmethoxypropanoyl]amino]-3-phenylmethoxypropanoyl]amino]-N-[(2S)-1-amino-1-oxopropan-2-yl]-3-hydroxypropanamide
• CAS: 849063-77-0
• 化学式: C₂₈H₃₇N₅O₈
• 分子量: 571.63
• InChiKey: LUZHQEDAHYVVQN-IMNFJDCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  198
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  AcNHSer(OBn)Ser(OBn)SerAlaCONH2 在 palladium on activated charcoal 四氮唑 、 氢气 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.0h， 生成 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-hydroxy-propionylamino)-3-hydroxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-hydroxy-phosphoryloxy}-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of Proteophosphoglycans of Leishmania major and Leishmania mexicana

  摘要：

  A novel approach for the synthesis of various fragments of proteophosphoglycans from Leishmania major and Leishmania mexicana proteophosphoglycans has been developed. These compounds have been obtained by coupling alpha-mannosyl and alpha-acetyl-glucosamine phosphoramidite derivatives with the serine hydroxyl of various amino acids and peptides to give, after oxidation with tert-BuOOH, phosphotriesters exclusively as alpha-anomers in good yield. The resulting compounds could be deblocked using conventional methods. Glycophosphorylation of preassembled and properly protected peptides was found to be more efficient for the preparation of proteophosphoglycan fragments than a building block approach strategy using a phosphoglycosylserine derivative.

  DOI：

  10.1021/jo048443z
• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-O-苄基-L-丝氨酸 、 FMOC-O-叔丁基-L-丝氨酸 生成 AcNHSer(OBn)Ser(OBn)SerAlaCONH2
  参考文献：
  名称：

  Synthesis of Proteophosphoglycans of Leishmania major and Leishmania mexicana

  摘要：

  A novel approach for the synthesis of various fragments of proteophosphoglycans from Leishmania major and Leishmania mexicana proteophosphoglycans has been developed. These compounds have been obtained by coupling alpha-mannosyl and alpha-acetyl-glucosamine phosphoramidite derivatives with the serine hydroxyl of various amino acids and peptides to give, after oxidation with tert-BuOOH, phosphotriesters exclusively as alpha-anomers in good yield. The resulting compounds could be deblocked using conventional methods. Glycophosphorylation of preassembled and properly protected peptides was found to be more efficient for the preparation of proteophosphoglycan fragments than a building block approach strategy using a phosphoglycosylserine derivative.

  DOI：

  10.1021/jo048443z

文献信息

• Synthesis of Proteophosphoglycans of <i>Leishmania </i><i>m</i><i>ajor</i> and <i>Leishmania </i><i>m</i><i>exicana</i>
  作者：Debatosh Majumdar、Galal A. Elsayed、Therese Buskas、Geert-Jan Boons

  DOI：10.1021/jo048443z

  日期：2005.3.1

  A novel approach for the synthesis of various fragments of proteophosphoglycans from Leishmania major and Leishmania mexicana proteophosphoglycans has been developed. These compounds have been obtained by coupling alpha-mannosyl and alpha-acetyl-glucosamine phosphoramidite derivatives with the serine hydroxyl of various amino acids and peptides to give, after oxidation with tert-BuOOH, phosphotriesters exclusively as alpha-anomers in good yield. The resulting compounds could be deblocked using conventional methods. Glycophosphorylation of preassembled and properly protected peptides was found to be more efficient for the preparation of proteophosphoglycan fragments than a building block approach strategy using a phosphoglycosylserine derivative.