CAS: 80126-51-8; H-Phe(3-Cl)-Oh

该化合物是一种非天然的氨基酸衍生物,在苯环的元体位置上具有氯替代物.这一修改增强了其在peptide合成和制药研究中的效用,在这种研究中,它作为引入卤化芳烃模型的多功能构件.氯组具有更大的消毒和电子效应,影响peptide的相容性和约束性互动.它与标准的固相基聚(SPPS)协议的高度纯度和兼容性使得它对于设计生物活性聚苯醚和改良蛋白具有价值.该化合物在药用化学中特别有用,用于促进结构-活动关系和开发有针对性的治疗方法.

结构式图片

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123053-22-5 80126-52-9 80102-25-6

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CAS号1866-38-2 间氯肉桂酸 | CAS号123052-80-2 (2S,5S)-tert-bu... | CAS号766-80-3 3-氯溴苄

合成工艺路线路线简述

  • 合成目标产物 L-3-Chlorophenylalanine 主要起始原料 3-Chlorobenzyl Bromide
  • (文献来源)合成步骤主要原料 3-Chlorobenzyl Bromide
3-氯苯丙氨酸置于phenylalanine Ammonia Lyase From Lettuce (Lactuca Sativa L.) Lspal3,Ammonium Carbamate体系中,用 甲醇,水 作为反应溶剂,化学反应 1.17H,反应生成 3-氯-L-苯丙氨酸
参考文献:生菜 (Lactuca Sativa L.) 苯丙氨酸氨裂解酶作为生产 D-和 L-氨基酸的稳健生物催化剂的表征
标题:生菜 (Lactuca Sativa L.) 苯丙氨酸氨裂解酶作为生产 D-和 L-氨基酸的稳健生物催化剂的表征
摘要:苯丙氨酸解氨酶 (Pal) 催化l-苯丙氨酸可逆转化为相应的反式肉桂酸,从而提供了一条获得光学纯 α-氨基酸的途径.我们探索了生菜(Lactuca Sativa L.)基因组中编码的所有五种 Pal 的催化功能,此前已知这些 Pal 与伤口褐变有关.所有ls Pal 在氨消除反应中均对l-苯丙氨酸具有活性,并在 55-60 oc 和 Ph 9.0-9.5 时表现出最大活性.然而,其中的四种(Ls Pal1-Ls Pal4)表现出比ls Pal5 显着更高的活性和热稳定性,以及更广泛的底物谱,包括一些具有空间要求或给电子取代基的具有挑战性的底物.对最好的ls Pal3 进行了一组 21 种外消旋苯丙氨酸衍生物的动力学拆分,以及 21 种肉桂酸衍生物的氨加成.它在大多数情况下表现出优异的对映选择性,并且对于许多具有挑战性的非天然底物,其活性明显优于之前描述的 Pal,这证明了其在生物催化方面的巨大潜力.
DOI:10.1021/acs.Jafc.2C07890

海关参考信息

专利信息


专利号:US-9938509-B2
优先权日:2010-12-08
标 题 :Biocatalysts and methods for the synthesis of armodafinil
发明人:ANG EE LUI; ALVIZO OSCAR; BEHROUZIAN BEHNAZ; CLAY MICHAEL D; COLLIER STEVEN J; EBERHARD ELLEN D; FAN FU; SONG SHIWEI; SMITH DEREK J; WIDEGREN MAGNUS; WILSON ROBERT; XU JUNYE; ZHU JUN
权利人:CODEXIS INC
摘要:The present invention relates to non-naturally occurring polypeptides useful for preparing armodafinil, polynucleotides encoding the polypeptides, and methods of using the polypeptides. The non-naturally occurring polypeptides of the present invention are effective in carrying out biocatalytic conversion of the (i) 2-(benzhydrylsulfinyl)acetamide to (−)-2-[(R)-(diphenylmethyl)sulfinyl]acetamide (armodafinil), or (ii) benzhydryl-thioacetic acid to (R)-2-(benzhydrylsulfinyl)acetic acid, which is a pivotal intermediate in the synthesis of armodafinil, in enantiomeric excess.

专利号:US-2023212788-A1
优先权日:2020-03-26
标 题:New method for automated on-demand biomolecular array synthesis
发明人:ZHANG YIXIN; LIN WEILIN
权利人:UNIV DRESDEN TECH
摘要:The invention provides an amphiphilic coating for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, comprising a hydrophilic chemical structure and a lipophilic group, wherein said peptides and small molecular compounds differ from spot to spot from each other in the chemical structure, characterized in that said amphiphilic coating possesses low wettability to polar aprotic solvents used in the array synthesis; said amphiphilic coating possessing low wettability is designed that it can be converted to a coating possessing high wettability by hydrolysis of the lipophilic group; and said amphiphilic coating comprises an amino group for the reaction with an electrophilic reagent. The invention further provides a solid support comprising said amphiphilic coating and a method for method for the direct and rapid synthesis of an array of peptides and small molecular compounds on a planar surface of a solid support, wherein said planar surface of a solid support comprises said amphiphilic coating. Said method includes the enhancing of the wettability of a glass surface to organic solvents to realize automated on-demand biomolecular array synthesis comprising both, peptides and small molecular compounds. The amphiphilic surface can be switched to a hydrophilic surface, resulting in high density arrays suitable for protein- and cell-based screening.

专利号:US-9663771-B2
优先权日:2013-01-18
标题 :Engineered biocatalysts useful for carbapenem synthesis
发明人:SUKUMARAN JOLY; SMITH DEREK; YANG HONG; YEO WAN LIN; MOORE JEFFREY C
权利人:CODEXIS INC
摘要:The present disclosure provides engineered pNB esterase polypeptides useful for the synthesis of the carbapenem antibiotic, imipenem. The disclosure also provides polynucleotides encoding the engineered pNB esterases, host cells capable of expressing the engineered pNB esterases, and methods of using the engineered pNB esterases in the production of imipenem.

专利号:US-2022243244-A1
优先权日:2019-10-10
标 题 :Compositions and methods for in vivo synthesis of unnatural polypeptides
发明人:ROMESBERG FLOYD E; FISCHER EMIL C; HASHIMOTO KOJI; FELDMAN AARON W; DIEN VIVIAN T; ZHANG YORKE
权利人:SCRIPPS RESEARCH INST
摘要:Disclosed herein are compositions, methods, and kits for a cell incorporating unnatural amino acids into an unnatural polypeptide. Also disclosed herein are compositions, methods, and kits for increasing activity and yield of the unnatural polypeptide synthesized by the cell.

专利号:US-2023037284-A9
优先权日:2018-11-30
标题:Combination therapy of peptidomimetic macrocycles
发明人:GUERLAVAIS VINCENT; ANNIS DAVID ALLEN
权利人:AILERON THERAPEUTICS INC
摘要:The present disclosure describes the synthesis of peptidomimetic macrocycles and methods of using peptidomimetic macrocycles to treat a condition. The present disclosure also describes methods of using peptidomimetic macrocycles in combination with at least one additional pharmaceutically-active agent for the treatment of a condition, for example, cancer.

专利号:US-9574189-B2
优先权日:2005-12-01
标题:Enzymatic encoding methods for efficient synthesis of large libraries
发明人:FRANCH THOMAS; LUNDORF MIKKEL DYBRO; JACOBSEN SØREN NYBOE; OLSEN EVA KAMPMANN; ANDERSEN ANNE LEE; HOLTMANN ANETTE; HANSEN ANDERS HOLM; SØRENSEN ANDERS MALLING; GOLDBECH ANNE; DE LEON DAEN; KALDOR DITTE KIEVSMOSE; SLØK FRANK ABILDGAARD; HUSEMOEN GITTE NYSTRUP; DOLBERG JOHANNES; Jensen Kim Birkebæ; PEDERSEN LENE; NØRREGAARD-MADSEN MADS; GODSKESEN MICHAEL ANDERS; GLAD SANNE SCHRØDER; NEVE SØREN; THISTED THOMAS; KRONBORG TINE TITILOLA AKINLEMINU; SAMS CHRISTIAN KLARNER; FELDING JAKOB; FRESKGÃ…RD PER-OLA; GOULIAEV ALEX HAAHR; PEDERSEN HENRIK
权利人:FRANCH THOMAS; LUNDORF MIKKEL DYBRO; JACOBSEN SØREN NYBOE; OLSEN EVA KAMPMANN; ANDERSEN ANNE LEE; HOLTMANN ANETTE; HANSEN ANDERS HOLM; SØRENSEN ANDERS MALLING; GOLDBECH ANNE; DE LEON DAEN; KALDOR DITTE KIEVSMOSE; SLØK FRANK ABILDGAARD; HUSEMOEN GITTE NYSTRUP; DOLBERG JOHANNES; Jensen Kim Birkebæ; PEDERSEN LENE; NØRREGAARD-MADSEN MADS; GODSKESEN MICHAEL ANDERS; GLAD SANNE SCHRØDER; NEVE SØREN; THISTED THOMAS; KRONBORG TINE TITILOLA AKINLEMINU; SAMS CHRISTIAN KLARNER; FELDING JAKOB; FRESKGÃ…RD PER-OLA; GOULIAEV ALEX HAAHR; PEDERSEN HENRIK; NUEVOLUTION AS
摘要:Disclosed is a method for obtaining a bifunctional complex comprising a molecule linked to a single stranded identifier oligonucleotide, wherein a nascent bifunctional complex comprising a chemical reaction site and a priming site for enzymatic addition of a tag is a) reacted at the chemical reaction site with one or more reactants, and b) reacted enzymatically at the priming site with one or more tag(s) identifying the reactant(s).
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主要参考文献

[参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-830.

合成参考文献


摘要:Nguyen, B. N.; Hii, K. K.; Szymański, W.; Janssen, D. B., Science of Synthesis: Stereoselective Synthesis, (2011) 1, 643.
摘要:Bartsch, S.; Vogel, A., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 302.
摘要:Parmeggiani, F.; Galman, J. L.; Montgomery, S. L.; Turner, N. J., Science of Synthesis, (2019) , 408.
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