(S)-3-氟丙氨酸 | 35455-20-0

• 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: (S)-3-氟丙氨酸
• 英文名称: (S)-3-fluoroalanine
• 英文别名: 3-fluoro-D-alanine；Fa；(2S)-2-azaniumyl-3-fluoropropanoate
• CAS: 35455-20-0
• 化学式: C₃H₆FNO₂
• 分子量: 107.085
• InChiKey: UYTSRQMXRROFPU-UWTATZPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-氟丙氨酸 、 N-苄氧羰基-L-丙氨酸 N-羟基琥珀酰亚胺酯 生成 N-carbobenzoxy-L-alanyl-β-fluoro-D-alanine
  参考文献：
  名称：

  CHU, D. T.;MARTIN, J. R.;THOMAS, A. M.;WIDEBURG, N. E.

  摘要：

  DOI：
• 作为产物：
  描述：

  D-丝氨酸 在 sulfur tetrafluoride 、 氢氟酸 作用下， 生成 (S)-3-氟丙氨酸
  参考文献：
  名称：

  Selective Fluorination of Hydroxy Amines and Hydroxy Amino Acids with Sulfur Tetrafluoride in Liquid Hydrogen Fluoride

  摘要：

  DOI：

  10.1021/jo00913a900
• 作为试剂：
  描述：

  4-羟基-二苯甲酮 在 palladium diacetate 、 sulfonyl chloride resin 、 TEA 、 (S)-3-氟丙氨酸 、 三乙胺 作用下， 生成 二苯甲酮
  参考文献：
  名称：

  Reductive cleavage of resin bound arylsulfonates

  摘要：

  A 4-hydroxybenzoate was tethered to a solid support via an arylsulfonate bond. The carboxylate functionality was converted to a variety of esters and amides. The products were then liberated from the resin by Pd(0) catalyzed reductive cleavage of the arylsulfonate oxygen. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00640-6

文献信息

• ω-Transaminase-catalyzed asymmetric synthesis of unnatural amino acids using isopropylamine as an amino donor
  作者：Eul-Soo Park、Joo-Young Dong、Jong-Shik Shin

  DOI：10.1039/c3ob40495a

  日期：——

  Isopropylamine is an ideal amino donor for reductive amination of carbonyl compounds by ω-transaminase (ω-TA) owing to its cheapness and high volatility of a ketone product. Here we developed asymmetric synthesis of unnatural amino acids via ω-TA-catalyzed amino group transfer between α-keto acids and isopropylamine.

  异丙基胺是Ï-反式胺酶（Ï-TA）对羰基化合物进行还原胺化反应的理想氨基供体，因为它价格低廉且酮产物挥发性高。在此，我们开发了通过Ï-TA催化的δ-酮酸和异丙胺之间的氨基转移不对称合成非天然氨基酸的方法。
• Kinetic aspects involved in the simultaneous enzymatic synthesis of (S)-3-fluoroalanine and (R)-3-fluorolactic acid
  作者：Luciana P.B. Gonçalves、O.A.C. Antunes、Gerson F. Pinto、Enrique G. Oestreicher

  DOI：10.1016/j.jfluchem.2003.08.009

  日期：2003.12

  enzymatic system for the simultaneous synthesis of (S)-3-fluoroalanine (1a) and (R)-3-fluorolactic acid (3) with l-ALADH and l-lactate dehydrogenase using rac-1 and NAD+. Analysis of isolated products revealed 1a in 60% yield and 86% ee and 3 in 80% yield and over 99% ee. Compounds 1a and 3 represent chiral building blocks for the synthesis of several products with pharmacological activity. The presence

  在存在和不存在产物的情况下，通过初始速率实验，研究了由I-丙氨酸脱氢酶（I-ALADH）催化的rac -3-氟丙氨酸（rac -1）的脱氨基氧化。获得了反应动力学参数的估计。反应机理是顺序有序的BiTer机理，其被过量的（S）-3-氟丙氨酸抑制。这项动力学研究是开发双酶系统的基础，该酶系统可同时用L-ALADH和L-乳酸脱氢酶合成（S）-3-氟丙氨酸（1a）和（R）-3-氟乳酸（3）。使用rac -1和NAD +。分离产物的分析表明，产率为60％，ee为86％的1a和产率为99％ee的80％的3。化合物1a和3代表用于合成几种具有药理活性的产物的手性结构单元。底物中氟原子的存在导致其在酶的活性位点更好的相互作用。
• Process for preparing 3-fluoro-D-alanine and its deutero analogs
  申请人：Merck & Co., Inc.

  公开号：US03976689A1

  公开（公告）日：1976-08-24

  3-Fluoro-D-alanine and its deutero analogs, which are potent antibacterial agents, are prepared from fluoropyruvic acid by asymmetric synthesis using an optically active amine such as D-.alpha.-methyl-benzylamine.

  3-氟-D-丙氨酸及其氘代物是强效抗菌剂，通过不对称合成从氟丙酸制备，使用手性胺如D-.alpha.-甲基苄胺。
• Characterization of d-amino acid aminotransferase from Lactobacillus salivarius
  作者：Jyumpei Kobayashi、Yasuhiro Shimizu、Yuta Mutaguchi、Katsumi Doi、Toshihisa Ohshima

  DOI：10.1016/j.molcatb.2013.04.013

  日期：2013.10

  We searched a UniProt database of lactic acid bacteria in an effort to identify D-amino acid metabolizing enzymes other than alanine racemase. We found a D-amino acid aminotransferase (D-AAT) homologous gene (UniProt ID: Q1WRM6) in the genome of Lactobacillus salivarius. The gene was then expressed in Escherichia coli, and its product exhibited transaminase activity between D-alanine and alpha-ketoglutarate. This is the first characterization of a D-AAT from a lactic acid bacterium. L. salivarius D-AAT is a homodimer that uses pyridoxal-5'-phosphate (PLP) as a cofactor; it contains 0.91 molecules of PLP per subunit. Maximum activity was seen at a temperature of 60 degrees C and a pH of 6.0. However, the enzyme lost no activity when incubated for 30 min at 30 degrees C and pH 5.5 to 9.5, and retained half its activity when incubated at pH 4.5 or 11.0 under the same conditions. Double reciprocal plots of the initial velocity and D-alanine concentrations in the presence of several fixed concentrations of alpha-ketoglutarate gave a series of parallel lines, which is consistent with a Ping-Pong mechanism. The K-m values for D-alanine and alpha-ketoglutarate were 1.05 and 3.78 mM, respectively. With this enzyme, D-allo-isoleucine exhibited greater relative activity than D-alanine as the amino donor, while alpha-ketobutylate, glyoxylate and indole-3-pyruvate were all more preferable amino acceptors than alpha-ketoglutarate. The substrate specificity of L. salivarius D-AAT thus differs greatly from those of the other D-AATs so far reported. (c) 2013 Elsevier B.V. All rights reserved.
• Gerus, I. I.; Yagupol'skii, Yu. L.; Kukhar, V. P., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 3.1, p. 465 - 468
  作者：Gerus, I. I.、Yagupol'skii, Yu. L.、Kukhar, V. P.、Boguslavskaya, L. S.、Chuvatkin, N. N.、et al.

  DOI：——

  日期：——