Z-D-Phe-OBn | 247259-40-1

• 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-D-Phe-OBn
• 英文别名: benzyl (2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 247259-40-1
• 化学式: C₂₄H₂₃NO₄
• 分子量: 389.451
• InChiKey: ILHGLRRAUKTLLN-JOCHJYFZSA-N

物化性质

• 沸点：
  566.7±50.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Z-D-Phe-OBn 在 10% Pd/C 、 1,4-环己二烯 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以100%的产率得到D-苯丙氨酸
  参考文献：
  名称：

  1,4-Cyclohexadiene with Pd/C as a rapid, safe transfer hydrogenation system with microwave heating

  摘要：

  A method for the rapid, safe hydrogenation of alkenes and deprotection of benzyl ethers and carboxybenzyl amides is described using catalytic transfer hydrogenation under microwave heating conditions. Commonly available Pd/C catalyst is extremely effective with 1,4-cyclohexadiene as the hydrogen transfer source. In general, the reactions are complete within five minutes at 100 degrees C. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.023
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 、 2,4-二氯苯甲醛 在 对甲苯磺酸 作用下， 以 三氯乙烷 为溶剂， 反应 18.0h， 生成 Z-D-Phe-OBn 、 cis-4-Benzyl-3-carbobenzyloxy-2-(2,4-dichlorophenyl)oxazolidinone 、 cis-4-Benzyl-3-carbobenzyloxy-2-(2,4-dichlorophenyl)oxazolidinone
  参考文献：
  名称：

  无环氨基酸的对映体烷基化

  摘要：

  描述了用于无环氨基酸（丙氨酸和苯丙氨酸）的烷基化的立体有择方法，其进行构型保留。该方法包括a）将氨基酸转化为主要的2-芳基-3-羰基苄氧基恶唑烷酮（2和8），b）用CH 3 I或PhCH 2 Br烯醇化钾烷基化，c）碱水解并氢解为得到烷基化的氨基酸。

  DOI：

  10.1016/s0040-4039(01)81432-5

文献信息

• Chemically Modified “Polar Patch” Mutants of Subtilisin in Peptide Synthesis with Remarkably Broad Substrate Acceptance: Designing Combinatorial Biocatalysts
  作者：Kazutsugu Matsumoto、Benjamin G. Davis、J. Bryan Jones

  DOI：10.1002/1521-3765(20020916)8:18<4129::aid-chem4129>3.0.co;2-v

  日期：2002.9.16

  L-amino acid esters but also D-amino acid esters as acyl donors with glycinamide to give the corresponding dipeptides in good yields. These powerful enzymes are also applicable to the coupling of L-amino acid acyl donors with alpha-branched acyl acceptor, L-alaninamide. Typical increases in isolated yields of dipeptides of 60-80 % over SBL-WT (e.g. 0 % yield of Z-D-Glu-GlyNH(2) using SBL-WT-->74 % using

  通过结合定点诱变和化学修饰以创建化学修饰的突变体（CMM）酶的策略，丝氨酸蛋白酶枯草杆菌蛋白酶（SBL）在肽合成中的适用性得到了显着提高。在主要特异性S（1）口袋底部的位置166处引入极性和/或同手性辅助取代基，例如X =恶唑烷酮，烷基铵基团和碳水化合物，创建了具有显着广泛的结构底物特异性的SBL CMM S166C-SX。这些CMM不仅能够催化作为酰基供体的L-氨基酸酯而且还与作为甘氨酸酰胺的D-氨基酸酯的偶联反应以良好的收率得到相应的二肽。这些强大的酶也适用于L-氨基酸酰基供体与α-支链酰基受体L-丙氨酰胺的偶联。与SBL-WT相比，二肽的分离产率通常提高60-80％（例如，使用SBL-WT的ZD-Glu-GlyNH（2）的产率为0％-使用S166C-S-（CH（2）的产率> 74％） （2）NMe（3）（+））展示了这种“极性补丁”策略的非凡合成实用性。此类广泛的系统显示出加宽的产品
• Glycosylation of the primary binding pocket of a subtilisin protease causes a remarkable broadening in stereospecificity in peptide synthesis
  作者：Kazutsugu Matsumoto、Benjamin G. Davis、J. Bryan Jones

  DOI：10.1039/b010021h

  日期：——

  Site-selective glycosylation at position 166 at the base of the primary specificity S1 pocket in the serine protease subtilisin Bacillus lentus (SBL) created glycoproteins that are capable of catalyzing the coupling reactions of not only L- amino acid esters but also D-amino acid esters to give the corresponding dipeptides in good yields as a result of greatly broadened substrate specificities that can be rationalized by the interaction of the glycans acting as chiral auxiliaries in stereochemically mismatched pairs.

  在丝氨酸蛋白酶枯草芽孢杆菌（SBL）主要特异性 S1 口袋底部的第 166 位进行位点选择性糖基化，生成的糖蛋白不仅能催化 L-氨基酸酯的偶联反应，还能催化 D-氨基酸酯的偶联反应，从而以良好的产量生成相应的二肽，这是因为底物的特异性大大提高了。
• Expanded structural and stereospecificity in peptide synthesis with chemically modified mutants of subtilisin
  作者：Kanjai Khumtaveeporn、Grace DeSantis、J.Bryan Jones

  DOI：10.1016/s0957-4166(99)00255-4

  日期：1999.7

  Employing the strategy of combined site directed mutagenesis and chemical modification, we previously generated chemically modified mutant enzymes (CMMs) of subtilisin Bacillus lentus (SBL). We now report the use of these SBL-CMMs for peptide coupling reactions. The SBL-CMMs exhibit dramatically altered substrate specificity, including the acceptance of d-amino acid acyl donors, generating dipeptides

  采用位点定向诱变和化学修饰相结合的策略，我们以前生成了枯草杆菌蛋白酶慢芽孢杆菌（SBL）的化学修饰突变酶（CMM ）。我们现在报告这些SBL-CMM用于肽偶联反应。SBL-CMMs表现出显着改变的底物特异性，包括接受d-氨基酸酰基供体，产生包含d-Phe，d-Ala和d-Glu的二肽，产率高达66％，这是使用野生型无法实现的SBL（WT-SBL）。另外，SBL-CMM在其S 1 '口袋中容纳α-支链氨基酸，例如l-Ala-NH 2作为酰基受体，而WT-SBL则不会。
• Modified enzymes and their use for peptide synthesis
  申请人：——

  公开号：US20020137177A1

  公开（公告）日：2002-09-26

  The present invention relates to modified enzymes with one or more amino acid residues from an enzyme being replaced by cysteine residues, where at least some of the cysteine residues are modified by replacing thiol hydrogen in the cysteine residue with a thiol side chain to form a modified enzyme, wherein the modified enzyme has high esterase and low amidase activity. Also, a method of producing the modified enzymes is provided. The present invention also relates to a method for using the modified enzymes in peptide synthesis.

  本发明涉及一种改性酶，其中酶中的一个或多个氨基酸残基被半胱氨酸残基替换，至少一些半胱氨酸残基通过将半胱氨酸残基中的硫醇氢替换为硫醇侧链而被改性，形成改性酶，其中改性酶具有高酯酶活性和低酰胺酶活性。同时，提供了一种生产改性酶的方法。本发明还涉及一种在肽合成中使用改性酶的方法。
• 1,4-Cyclohexadiene with Pd/C as a rapid, safe transfer hydrogenation system with microwave heating
  作者：John F. Quinn、Dana A. Razzano、Kathryn C. Golden、Brian T. Gregg

  DOI：10.1016/j.tetlet.2008.08.023

  日期：2008.10

  A method for the rapid, safe hydrogenation of alkenes and deprotection of benzyl ethers and carboxybenzyl amides is described using catalytic transfer hydrogenation under microwave heating conditions. Commonly available Pd/C catalyst is extremely effective with 1,4-cyclohexadiene as the hydrogen transfer source. In general, the reactions are complete within five minutes at 100 degrees C. (c) 2008 Elsevier Ltd. All rights reserved.