N-(4-Phenylacetoxybenzyloxycarbonyl)-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine(O-tert-butyl) | 229345-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-Phenylacetoxybenzyloxycarbonyl)-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine(O-tert-butyl)
• 英文别名: (2S)-2-[[(2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-[[4-(2-phenylacetyl)oxyphenyl]methoxycarbonylamino]propanoyl]amino]-3-[(2-methylpropan-2-yl)oxy]propanoic acid
• CAS: 229345-02-2
• 化学式: C₄₀H₅₁N₃O₁₇
• 分子量: 845.855
• InChiKey: FNPKADTVYXELGN-XHGYPYSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  60
• 可旋转键数：
  25
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  267
• 氢给体数：
  4
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  N-(4-Phenylacetoxybenzyloxycarbonyl)-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine(O-tert-butyl) 在 penicilin G acylase 、 水 、 1-羟基苯并三唑 、 sodium iodide 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-Allyloxycarbonyl-L-threonyl(O-diallylphosphato)-L-glutaminyl-L-threonyl-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-seryl(O-tert-butyl)-L-seryl(O-tert-butyl)-glycine tert-butyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of a Characteristic Glycophosphopeptide from the Transactivation Domain of the Serum Response Factor

  摘要：

  Glycopeptides, phosphopeptides, and glycophosphopeptides can be synthesized efficiently by a strategy based on a combination of suitable enzyme-labile protecting groups. Thus, probes for biological studies can be accessed. An example is the glycosylated and phosphorylated heptapeptide 1 from the transactivation domain of the human serum response factor, which contains an additional biotin label for detection with streptavidin.

  DOI：

  10.1002/(sici)1521-3773(19990503)38:9<1250::aid-anie1250>3.0.co;2-m
• 作为产物：
  描述：

  N-(4-Phenylacetoxybenzyloxycarbonyl)-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine(O-tert-butyl) choline ester bromide 在 butyrylcholine esterase 作用下， 以 phosphate buffer 为溶剂， 反应 72.0h， 以65%的产率得到N-(4-Phenylacetoxybenzyloxycarbonyl)-L-seryl(O-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-serine(O-tert-butyl)
  参考文献：
  名称：

  Enzymatic Protecting Group Techniques for Glyco- and Phosphopeptide Chemistry: Synthesis of a Glycophosphopeptide from Human Serum Response Factor

  摘要：

  The covalent modification of proteins by phosphorylation and by glycosylation with GlcNAc residues are important regulatory processes which mediate biological signal transduction. For the study of such biological phenomena in molecular detail characteristic peptides which embody both types of modification may serve as efficient tools. However, their synthesis is complicated by their pronounced acid and base lability as well as their multifunctionality. For this purpose the enzyme labile choline ester was developed. The choline ester can be removed selectively and in high yields from various GlcNAc-glycopeptides and phosphopeptides at pH 6.5 and 37 degrees C. The conditions under which the enzymatic deprotections proceed are so mild that no undesirable side reactions are observed (i.e., no cleavage or anomerization of the glycosidic bonds and no beta-elimination of the phosphate or the carbohydrate occur). The specificity of the biocatalyst guarantees that neither the peptide bonds nor the other protecting groups present are being attacked. When this enzymatic protecting group technique was combined with the enzyme-labile 4-(phenylacetoxy)benzyloxycarbonyl (PhAcOZ) urethane protecting group a complex glycophosphopeptide could be built up. The glycopeptide is equipped with a biotin label by which it can be traced in biological systems. This peptide represents a characteristic partial structure of a glycosylated and phosphorylated sequence from the transactivation domain of serum response factor (SRF), a widely occuring human transcription factor.

  DOI：

  10.1002/(sici)1521-3765(20000502)6:9<1564::aid-chem1564>3.3.co;2-h