Ac-Ala-N^α-Me-Ser[β-Gal(OAc)4]-Phe-NH2 | 291311-52-9

• 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: Ac-Ala-N^α-Me-Ser[β-Gal(OAc)4]-Phe-NH2
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2S)-2-[[(2S)-2-acetamidopropanoyl]-methylamino]-3-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-oxopropoxy]-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 291311-52-9
• 化学式: C₃₂H₄₄N₄O₁₄
• 分子量: 708.72
• InChiKey: NQMFEBYLZWXBQR-QXAKPXNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  245
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Ac-Ala-N^α-Me-Ser[β-Gal(OAc)4]-Phe-NH2 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 N^α-acetyl-L-alanyl-(2-aminoprop-2-enoyl)-L-phenylalanine amide 、 (2S)-2-[[(2S)-2-[[(2S)-2-acetamidopropanoyl]-methylamino]-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanoyl]amino]-3-phenylpropanamide
  参考文献：
  名称：

  Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine

  摘要：

  Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00611-0
• 作为产物：
  描述：

  Fmoc-N-methyl-L-serine 在 三氟化硼乙醚 、 达卡巴嗪 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Ac-Ala-N^α-Me-Ser[β-Gal(OAc)4]-Phe-NH2
  参考文献：
  名称：

  Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine

  摘要：

  Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00611-0