Z-Ser-Ala-OtBu | 24864-42-4

• 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: Z-Ser-Ala-OtBu
• 英文别名: Cbz-Ser-Ala-O^tBu；tert-butyl (2S)-2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 24864-42-4
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: YBZGWUMKDYEHHU-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-Ser-Ala-OtBu 在 palladium on activated charcoal 吡啶 、 四(三苯基膦)钯 、 4 A molecular sieve 、 氢气 、 氰化汞 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 丙二酸二甲酯 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 108.0h， 生成 N-benzyloxycarbonyl-alanyl--seryl-alanine tert-butyl ester
  参考文献：
  名称：

  Synthetic O-glycopeptides as model substrates for glycosyltransferases

  摘要：

  A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives as acceptors. The urethane group is easily exchanged for the natural N-acetyl moiety and O-deacetylation is achieved with hydrazine/methanol. The resulting O-GlcNAc derivatives are subjected to an enzymatic galactosylation procedure using beta-1,4-galactosyluwsferase (EC 2.4.1.22) to furnish O-glycopeptides of the neolactosamine type.

  DOI：

  10.1016/s0957-4166(00)80230-x
• 作为产物：
  描述：

  L-丙氨酸叔丁酯盐酸盐 在 2-溴-4-(三氟甲基)苯硼酸 、 sodium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.08h， 生成 Z-Ser-Ala-OtBu
  参考文献：
  名称：

  通过硼酸催化从α-氨基酸衍生的惰性酯形成羟基引导的肽键

  摘要：

  描述了硼酸催化 α-氨基酸甲酯形成肽键。该催化对 β-羟基-α-氨基酯表现出高化学选择性，使肽具有高至优异的产率和高官能团耐受性。这种羟基定向的肽键形成可适用于寡肽合成。这是有机硼催化α-氨基酸衍生的惰性酯形成肽键的第一个成功例子。

  DOI：

  10.1039/d3cc04856j

文献信息

• Glycoside synthesis via electrophile-induced activation of N-allyl carbamates
  作者：Horst Kunz、Jörg Zimmer

  DOI：10.1016/s0040-4039(00)60478-1

  日期：1993.4

  O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.

  由未保护的单糖和异氰酸烯丙酯得到的O-苄基，O-酰基，N-酰基和异亚丙基保护的糖基N-烯丙基氨基甲酸酯，通过亲电试剂诱导的环化反应活化，并与羟基化合物反应形成相应的糖苷。
• Diboronic Acid Anhydride-Catalyzed Direct Peptide Bond Formation Enabled by Hydroxy-Directed Dehydrative Condensation
  作者：Masayoshi Koshizuka、Kazuishi Makino、Naoyuki Shimada

  DOI：10.1021/acs.orglett.0c03252

  日期：2020.11.6

  We report the catalytic direct peptide bond formations via dehydrative condensation of β-hydroxy-α-amino acids, affording the serine, threonine, or β-hydroxyvaline-derived peptides in high to excellent yields with high functional group tolerance, minimum epimerization, and excellent chemoselectivity. The key to the success of these atom-economical transformations is the use of diboronic acid anhydride catalyst for the hydroxy-directed reactions.
• Enzymatic glycosylation of o-glycopeptides
  作者：Michael Schultz、Horst Kunz

  DOI：10.1016/s0040-4039(00)79082-4

  日期：1992.9

  O-Glycosylation of serine derivatives carried out with N-urethane protected glucosamine yields O-glycopeptides which are regio-and stereoselectively galactosylated with the aid of beta-1,4-galactosyltransferase (EC2.4.1.22).
• Synthetic O-glycopeptides as model substrates for glycosyltransferases
  作者：Michael Schultz、Horst Kunz

  DOI：10.1016/s0957-4166(00)80230-x

  日期：1993.6

  A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives as acceptors. The urethane group is easily exchanged for the natural N-acetyl moiety and O-deacetylation is achieved with hydrazine/methanol. The resulting O-GlcNAc derivatives are subjected to an enzymatic galactosylation procedure using beta-1,4-galactosyluwsferase (EC 2.4.1.22) to furnish O-glycopeptides of the neolactosamine type.
• Hydroxy-directed peptide bond formation from α-amino acid-derived inert esters enabled by boronic acid catalysis
  作者：Naoya Takahashi、Airi Takahashi、Naoyuki Shimada

  DOI：10.1039/d3cc04856j

  日期：——

  acid-catalyzed peptide bond formation from α-amino acid methyl esters is described. The catalysis showed high chemoselectivity for β-hydroxy-α-amino esters, affording the peptides in high to excellent yields with high functional group tolerance. This hydroxy-directed peptide bond formation could be applicable to oligopeptide syntheses. This is the first successful example of organoboron-catalyzed peptide bond

  描述了硼酸催化 α-氨基酸甲酯形成肽键。该催化对 β-羟基-α-氨基酯表现出高化学选择性，使肽具有高至优异的产率和高官能团耐受性。这种羟基定向的肽键形成可适用于寡肽合成。这是有机硼催化α-氨基酸衍生的惰性酯形成肽键的第一个成功例子。