Ac-Tyr-Ala-NH2 | 29701-42-6

• 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-Tyr-Ala-NH2
• 英文别名: N^α-acetyl-S-Tyr-S-AlaNH2；N-Acetyl-L-tyrosyl-L-alaninamide；(2S)-2-acetamido-N-[(2S)-1-amino-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide
• CAS: 29701-42-6
• 化学式: C₁₄H₁₉N₃O₄
• 分子量: 293.323
• InChiKey: MYBDZLXDTGBTJT-UFBFGSQYSA-N

物化性质

• 沸点：
  723.7±60.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ac-Tyr-Ala-NH2 在 水 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以15.5%的产率得到Ac-Tyr-Ala-OH
  参考文献：
  名称：

  Cerovsky, Vaclav; Martinek, Karel, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 2027 - 2041

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰-L-酪氨酸乙酯 、 2-氨基丙酰胺 在 bicarbonate buffer 、 bovine α-chymotrypsin (EC 3.4.21.1) 作用下， 生成 Ac-Tyr-Ala-NH2
  参考文献：
  名称：

  Determination of the Enantioselectivity for Kinetically Controlled Condensations Catalysed by Amidases and Peptidases

  摘要：

  For kinetically controlled synthetic reactions catalysed by amidases and peptidases, the enantio- or stereoselectivity determined from initial rates with racemic mixtures (E-syn,E-rac) was found to differ from the enantioselectivity determined from measurements with isolated enantiomeric nucleophiles (E-syn). This was observed for kinetically controlled condensation of R-phenyglycineamide with S-, R- and racemic Phe and S-, R- and racemic Leu catalysed by penicillin amidase from E. coli and for kinetically controlled condensation of N-alpha-acetyl-S-tyrosine ethyl ester with S-, R- and racemic AlaNH(2) catalysed by bovine alpha-chymotrypsin. It is shown that only E-syn,E-rac determined with racemic, nucleophiles is an intrinsic enzyme property which should be used to study the influence of the primary structure, physicochemical parameters and immobilisation on biocatalyst enantioselectivity in kinetically controlled synthetic reactions catalysed by these enzymes.

  DOI：

  10.1002/1615-4169(200212)344:10<1115::aid-adsc1115>3.0.co;2-d

文献信息

• Photoredox Ni-catalyzed peptide C(sp²)–O cross-coupling: from intermolecular reactions to side chain-to-tail macrocyclization
  作者：Hyelee Lee、Nicolas C. Boyer、Qiaolin Deng、Hai-Young Kim、Tomi K. Sawyer、Nunzio Sciammetta

  DOI：10.1039/c9sc00694j

  日期：——

  Ni/photoredox (4DPAIPN) dual catalysis enabled challenging peptide C(sp2)–O coupling reactions. Successful cross-coupling reactions were demonstrated with highly functionalized alcohols including side chains of amino acids (i.e., serine, threonine, tyrosine), trans-4-hydroxy-L-proline, alkyl alcohols, alkynylated alcohols, and carbohydrates. Coupling reactions between bromobenzoyl-capped peptides containing

  Ni/光氧化还原 (4DPAIPN) 双重催化实现了具有挑战性的肽 C(sp 2 )–O 偶联反应。使用包括氨基酸侧链(即，丝氨酸、苏氨酸、酪氨酸)、反式-4-羟基-L-脯氨酸、烷基醇、炔基化醇和碳水化合物的高度官能化的醇证明了成功的交叉偶联反应。含有各种侧链的溴苯甲酰基封端的肽与受保护的丝氨酸结构单元或含丝氨酸的二肽之间的偶联反应也有效地进行。在 C 端伯酰胺存在的情况下，在分子间反应中实现了化学选择性 C-O 偶联（通过 C-N）。此外，通过明智的结构设计与计算模型相结合，我们通过C-O偶联证明了含有β-转角基序的肽的侧链到尾部大环化。这项工作中开发的方法为复杂的线性和大环肽的后期多样化带来了新的机会。
• RICCA, J. M.;CROUT, D. H. G., J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N1, C. 2126-2127
  作者：RICCA, J. M.、CROUT, D. H. G.

  DOI：——

  日期：——
• Cerovsky, Vaclav; Martinek, Karel, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 7, p. 2027 - 2041
  作者：Cerovsky, Vaclav、Martinek, Karel

  DOI：——

  日期：——
• Determination of the Enantioselectivity for Kinetically Controlled Condensations Catalysed by Amidases and Peptidases
  作者：Boris Galunsky、Volker Kasche

  DOI：10.1002/1615-4169(200212)344:10<1115::aid-adsc1115>3.0.co;2-d

  日期：2002.12

  For kinetically controlled synthetic reactions catalysed by amidases and peptidases, the enantio- or stereoselectivity determined from initial rates with racemic mixtures (E-syn,E-rac) was found to differ from the enantioselectivity determined from measurements with isolated enantiomeric nucleophiles (E-syn). This was observed for kinetically controlled condensation of R-phenyglycineamide with S-, R- and racemic Phe and S-, R- and racemic Leu catalysed by penicillin amidase from E. coli and for kinetically controlled condensation of N-alpha-acetyl-S-tyrosine ethyl ester with S-, R- and racemic AlaNH(2) catalysed by bovine alpha-chymotrypsin. It is shown that only E-syn,E-rac determined with racemic, nucleophiles is an intrinsic enzyme property which should be used to study the influence of the primary structure, physicochemical parameters and immobilisation on biocatalyst enantioselectivity in kinetically controlled synthetic reactions catalysed by these enzymes.