(alphaR)-alpha-(乙酰氨基)-苯丁酸 | 5440-40-4

• 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
• 中文名称: (alphaR)-alpha-(乙酰氨基)-苯丁酸
• 中文别名: 乙酰-D-高苯丙氨酸
• 英文名称: (2R)-N-acetyl-2-amino-4-phenylbutyric acid
• 英文别名: (R)-N-acetyl-homophenylalanine；D-N-acetylhomophenylalanine；(R)-2-acetylamino-4-phenyl-butyric acid；(R)-2-Acetamino-4-phenyl-buttersaeure；linksdrehende α-Acetamino-γ-phenyl-buttersaeure；(R)-2-Acetylamino-4-phenyl-buttersaeure；Acetyl-D-Homophenylalanine；(2R)-2-acetamido-4-phenylbutanoic acid
• CAS: 5440-40-4；60505-02-4；96613-91-1；63393-59-9
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: CNQZAOFOKXXEOB-LLVKDONJSA-N

物化性质

• 沸点：
  461.1±38.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (alphaR)-alpha-(乙酰氨基)-苯丁酸 在 盐酸 作用下， 以96%的产率得到D-苯基丁氨酸
  参考文献：
  名称：

  血管紧张素转化酶抑制剂的研究。VI。吡虫啉二羧酸衍生物及其非对映异构体的合成及其对血管紧张素转化酶的抑制活性。

  摘要：

  合成了所有可能的二羧酸（10a）的非对映异构体（吡虫啉的生物活性形式），并检查了它们对血管紧张素转化酶（ACE）的抑制活性。这些化合物的体外ACE抑制活性很大程度上取决于每个分子中三个不对称碳的构型。（S，S，S）异构体（10a）的活性比其他异构体强得多。

  DOI：

  10.1248/cpb.40.1619
• 作为产物：
  描述：

  5-phenylethyl-imidazolidine-2,4-dione 在 CoCl₂ sodium hydroxide 、 potassium phosphate buffer 、 beef kidney acetone 作用下， 以 水 为溶剂， 反应 29.0h， 生成 (alphaR)-alpha-(乙酰氨基)-苯丁酸
  参考文献：
  名称：

  Enzymatic resolution of N-acetyl-homophenylalanine with mammalian kidney acetone powders

  摘要：

  Kidney acetone powders (KAP) from beef, dog, hog, rat, and sheep have been evaluated for resolving N-acetyl-DL-homophenylalanine. We also propose a simple protocol for the preparation of both enantiomers of homophenylalanine by enzymatic resolution using mammalian KAP. The beef kidney afforded the best results, rendering the highest isolated yields, 37.5% and 41% and enantiomeric excesses of 94% and >99% for both D-N-Ac-homophenylalanine and L-homophenylalanine, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.026

文献信息

• Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
  作者：Haruki Inada、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.8b03910

  日期：2019.2.1

  of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study

  已经开发了一种实用的伸缩三步法，用于从相应的1,2-二醇合成α-氨基酸。该方法能够直接合成游离的α-氨基酸，而无需任何保护/脱保护步骤。该方法对于制备15 N标记的α-氨基酸也是有效的。带有α，β-不饱和酯部分的1,2-二醇通过分子内[3 + 2]环加成反应提供双环α-氨基酸。初步研究表明，所得的α-氨基酸几乎可以完全被氨基酰基分解。
• Topical composition comprising N-acetylaldosamines or N-acetylamino acids
  申请人：Yu, Ruey J., Dr.

  公开号：EP1639994A2

  公开（公告）日：2006-03-29

  Compositions comprising N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl compounds are useful to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors. N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl composition may further comprise a cosmetic, pharmaceutical or other topical agent to enhance or create synergetic effects.

  包含 N-乙酰-醛胺，N-乙酰基氨基酸和相关 N-乙酰基化合物的组合物可用于缓解或改善各种美容状况和皮肤病，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及由外在因素引起的变化或损伤。N-acetyl-aldosamines, N-acetylamino acids 和相关的 N-acetyl 组合物可进一步包含化妆品、药物或其他外用制剂，以增强或产生协同效应。
• Topical composition comprising n-acetylaldosamines or n-acetylamino acids
  申请人：Yu, Ruey J.

  公开号：EP2080504A2

  公开（公告）日：2009-07-22

  Compositions comprising N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl compounds are useful to alleviate or improve various cosmetic conditions and dermatological disorders, including changes or damage to skin, nail and hair associated with intrinsic aging and/or extrinsic aging, as well as changes or damage caused by extrinsic factors. N-acetyl-aldosamines, N-acetylamino acids, and related N-acetyl composition may further comprise a cosmetic, pharmaceutical or other topical agent to enhance or create synergetic effects.

  包含 N-乙酰-醛胺，N-乙酰基氨基酸和相关 N-乙酰基化合物的组合物可用于缓解或改善各种美容状况和皮肤病，包括与内在老化和/或外在老化相关的皮肤、指甲和头发的变化或损伤，以及由外在因素引起的变化或损伤。N-acetyl-aldosamines, N-acetylamino acids 和相关的 N-acetyl 组合物可进一步包含化妆品、药物或其他外用制剂，以增强或产生协同效应。
• Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine
  作者：Bhalchandra K. Vaidya、Suyog S. Kuwar、Sandeep B. Golegaonkar、Sanjay N. Nene

  DOI：10.1016/j.molcatb.2011.10.003

  日期：2012.2

  L-Aminoacylase from Aspergillus melleus was co-aggregated with polyethyleneimine and subsequently cross-linked with glutaraldehyde to obtain aminoacylase-polyethyleneimine cross-linked enzyme aggregates (termed as AP-CLEA). Under the optimum conditions, AP-CLEA expressed 74.9% activity recovery and 81.2% aggregation yield. The said method of co-aggregation and cross-linking significantly improved the catalytic stability of L-aminoacylase with respect to temperature and storage. AP-CLEA were employed for enantioselective synthesis of three unnatural amino acids (namely: phenylglycine, homophenylalanine and 2-naphthylalanine) via chiral resolution of their ester-. amide- and N-acetyl derivatives. The enantioselectivity of AP-CLEA was the highest for hydrolysis of amino acid amides; was moderate for hydrolysis of N-acetyl amino acids and was the least for hydrolysis of amino acid esters. Furthermore, AP-CLEA were found to retain more than 92% of the initial activity after five consecutive batches of (RS)-homophenylalanine hydrolysis suggesting an adequate operational stability of the biocatalyst. (C) 2011 Elsevier B.V. All rights reserved.
• du Vigneaud; Wood; Irish, Journal of Biological Chemistry, 1939, vol. 129, p. 171,173
  作者：du Vigneaud、Wood、Irish

  DOI：——

  日期：——