DL-苯丙氨酸苄酯 | 47004-38-6

• 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
• 中文名称: DL-苯丙氨酸苄酯
• 英文名称: D-phenylalanine benzyl ester
• 英文别名: benzyl (2R)-2-amino-3-phenylpropanoate
• CAS: 47004-38-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: FPRSPUHXEPWUBZ-OAHLLOKOSA-N

物化性质

• 沸点：
  382.8±27.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  DL-苯丙氨酸苄酯 在 Streptomyces spp. 82F₂ D-aminopeptidase 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 D-苯丙氨酸
  参考文献：
  名称：

  Aminolytic reaction catalyzed by d-stereospecific amidohydrolases from Streptomyces spp

  摘要：

  From investigation of 2000 soil isolates, we identified two serine-type amidohydrolases that can hydrolyze D-aminoacyl derivatives from the culture supernatant of Streptomyces species 82F2 and 83D12. The enzymes, redesignated as 82F2-DAP and 83D12-DAP, were purified for homogeneity and characterized. Each enzyme had molecular mass of approximately 40 kDa, and each showed moderate stability with respect to temperature and pH. Among hydrolytic activities toward D-aminoacyl-pNAs, the enzymes showed strict specificity toward D-Phe-pNA, but showed broad specificity toward D-aminoacyl esters. The specific activity for D-Phe-pNA hydrolysis of 82F2-DAP was ten-fold higher than that of 83D12-DAP. As a second function, each enzyme showed peptide bond formation activity by its function of aminolysis reaction. Based on results of D-Phe D-Phe synthesis under various conditions, we propose a reaction mechanism for D-Phe D-Phe production. Furthermore, the enzymes exhibited peptide elongation activity, producing oligo homopeptide in a one-pot reaction. We cloned the genes encoding each enzyme, which revealed that the primary structure of each enzyme showed 30-60% identity with those of peptidases belonging to the clan SE, S12 peptidase family categorized as serine peptidase with D-stereospecificity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2011.04.020
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 在 caesium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 DL-苯丙氨酸苄酯
  参考文献：
  名称：

  Peptide nucleic acids (PNAs) with a functional backbone

  摘要：

  The synthesis of 10 new T-PNA monomers derived from L-amino acids is presented. The monomers were incorporated into decameric PNA oligomers, and the hybridisation with RNA, DNA and PNA complements studied by thermal stability measurements. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00862-4

文献信息

• Macrocyclic Modulators of the Ghrelin Receptor
  申请人：Ocera Therapeutics, Inc.

  公开号：US20180110824A1

  公开（公告）日：2018-04-26

  The present invention provides novel conformationally-defined macrocyclic compounds that have been demonstrated to be selective modulators of the ghrelin receptor (growth hormone secretagogue receptor, GHS-R1a and subtypes, isoforms and variants thereof). Methods of synthesizing the novel compounds are also described herein. These compounds are useful as agonists of the ghrelin receptor and as medicaments for treatment and prevention of a range of medical conditions including, but not limited to, metabolic and/or endocrine disorders, gastrointestinal disorders, cardiovascular disorders, obesity and obesity-associated disorders, central nervous system disorders, genetic disorders, hyperproliferative disorders and inflammatory disorders.

  本发明提供了一种新颖的构象定义明确的大环化合物，已经证明是生长激素分泌素受体（GHS-R1a及其亚型、异构体和变体）的选择性调节剂。本文还描述了合成这些新型化合物的方法。这些化合物可用作生长激素分泌素受体的激动剂，用于治疗和预防一系列医疗状况，包括但不限于代谢和/或内分泌紊乱、胃肠道紊乱、心血管疾病、肥胖和与肥胖相关的疾病、中枢神经系统疾病、遗传疾病、过度增殖性疾病和炎症性疾病。
• Inhibitors of human renin. Cyclic peptide analogs containing a D-Phe-Lys-D-Trp sequence
  作者：Anand S. Dutta、James J. Gormley、Peter F. McLachlan、John S. Major

  DOI：10.1021/jm00171a034

  日期：1990.9

  these compounds. Reducing the ring size gave much less potent compounds. The most potent analogue of the series, CO(CH2)2CHPhCO-D-Phe-Lys-D-Trp-NH(CH2)2CHMe (14, IC50 = 26 nM), was obtained by substituting the methylene group nearer to the D-Phe residue by a -CHPh- group. Compound 14 was 15-fold more potent in inhibiting human renin than porcine renin.

  已经合成了含有D-苯丙氨酸和D-色氨酸残基的环肽，并测试了其作为人肾素的抑制剂。其中大多数是CO（CH2）3CO-D-Phe-Lys-D-Trp-型或CO NH CO-Dhe-Lys-D-Trp-型的三肽衍生物，其中各个侧链亚甲基已被取代-CHMe-，-CMe2-，-CH（Ph）-，-CH（ Ph）-或-CH [ ）2CHMe2）-基团。这三个氨基酸残基和环的大小是这些化合物非常重要的特征。减小环的大小得到的有效化合物少得多。该系列最有效的类似物CO（ ）2CHPhCO-D-Phe-Lys-D-Trp-NH（ ）2CHMe（14，IC50 = 26 nM）通过取代更靠近D-的亚甲基获得-CHPh-基团的Phe残基。化合物14在抑制人肾素方面的效力比猪肾素高15倍。
• Synthesis of (S)- and (R)- tert Leucine Enabling Direct Coupling with α-Amino Acid Esters via β-Lactam-Derived α-Amino Acid N-Carboxy Anhydrides.
  作者：Claudio Palomo*、Iñaki Ganboa、Beatriz Odriozola、Anthony Linden

  DOI：10.1016/s0040-4039(97)00553-4

  日期：1997.4

  (3S, 4R)- and (3R, 4S)-3-hydroxy-4- tert-butyl β-lactams on exposure to 1M NaOCl and a catalytic amount of 2,2,6,6-tetramethylpiperidinyl-1-oxyl (TEMPO) afforded α-amino acid N-carboxy anhydrides formally derived from both (S)- and (R)- tert-leucine amino acids. © 1997 Published by Elsevier Science Ltd.

  （3S，4R）-和（3R，4S）-3-羟基-4-叔丁基β-内酰胺暴露于1M NaOCl和催化量的2,2,6,6-四甲基哌啶基-1-氧基（TEMPO ）得到形式上衍生自（S）-和（R）-叔亮氨酸氨基酸的α-氨基酸N-羧基酸酐。©1997由Elsevier Science Ltd发布。
• Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from <scp>d</scp>-Phenylalanine and (1<i>S</i>,2<i>S</i>)-(+)-1,2-Diaminocyclohexane via ¹H NMR Spectroscopy
  作者：Lei Feng、Guangpeng Gao、Hongmei Zhao、Li Zheng、Yu Wang、Pericles Stavropoulos、Lin Ai、Jiaxin Zhang

  DOI：10.1021/acs.joc.8b02212

  日期：2018.11.16

  Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1–G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a–1d has been synthesized from d-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1–G9

  以d-和l -α-氨基酸为客体，制备了一系列具有三个立体中心(±) -G1 - G9的三肽衍生物的对映体，并通过1 H NMR光谱进行手性识别。同时，由d-苯丙氨酸和 (1 S ,2 S )-(+)-1,2-二氨基环己烷合成了一系列四氮杂大环手性溶剂化剂 (TAMCSA) 1a – 1d 。(±) -G1 – G9的对映体鉴别是在 TAMCSA 1a – 1d存在下通过1 H NMR 光谱进行的。结果表明，在 TAMCSA 1a – 1d存在的情况下，可以通过多个质子的1 H NMR 信号有效地区分 (±)- G1 – G9的对映体，这些质子表现出高达 0.616 ppm 的不等价化学位移 (ΔΔδ)。此外，通过将分裂的相应质子的1 H NMR 信号与归因于单一对映体的信号进行比较，可以轻松指定(±) -G1 – G9的对映体。在 TAMCSA 1a – 1d存在的情况下，分别清楚地观察和计算了G1的不同光学纯度（ee
• Enantioselective Fluorescence Sensing of Amino Acids by Modified Cyclodextrins: Role of the Cavity and Sensing Mechanism
  作者：Sara Pagliari、Roberto Corradini、Gianni Galaverna、Stefano Sforza、Arnaldo Dossena、Marco Montalti、Luca Prodi、Nelsi Zaccheroni、Rosangela Marchelli

  DOI：10.1002/chem.200305448

  日期：2004.6.7

  ligand N(alpha)-[(5-dimethylamino-1-naphthalenesulfonyl)aminoethyl]-N(1)-propyl-phenylal aninamide, which has the same binding site and absolute configuration as 4, showed very low chiral discrimination ability. The enantioselectivity in fluorescence response was found to be due to the formation of diastereomeric ternary complexes, which were detected by ESI-MS and by circular dichroism. Time-resolved

  D-或L-氨基酸的添加诱导荧光强度的增加，这取决于所使用的氨基酸，并且在某些情况下取决于其绝对构型。发现环糊精4比3具有更高的对映选择性，这表明在环糊精腔中的自包含强烈增强了铜（II）配合物的手性识别能力。因此，具有与4相同的结合位点和绝对构型的线性荧光配体Nα-[（5-二甲基氨基-1-萘磺酰基）氨基乙基] -N（1）-丙基-苯基茴香胺显示出非常低的手性辨别能力。发现荧光响应中的对映选择性是由于非对映异构三元复合物的形成，其通过ESI-MS和圆二色性检测。