CAS: 149597-92-2; (S)-2-Amino-3,3-Diphenylpropanoic Acid

该化合物是一种非蛋白性非氨基酸,其特征是二苯代丙酸脊椎,该化合物因其立体化学纯度和结构僵硬性,成为不对称合成和药物研究的宝贵组成部分.两个苯基组的存在会增加消毒性障碍,有助于研究酶基相互作用或设计消化器.其高对应性纯度确保了对立体选择性反应的精确控制,而芳香环则有可能在分子识别中进行--的相互作用.应用包括开发生物活性化合物,手动催化剂和用于不对称转化的专门皮层.该化合物通常会得到严格的分析验证,以确保研究和工业环境的一致性.

结构式图片

相似化合物

138662-62-1 138662-63-2 143060-31-5

欧盟法规

ECHA物质C&L通报

上下游产品

L-3,3-diphenylalaninesultam hydr°Chloride diphenylchloromethane N-(diphenylmethylene)-L-3,3-diphenylalaninesultam Bromodiphenylmethane (S)-2-((methoxycarbonyl)amino)-3,3-diphenylpropanoic acid (1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester (2S)-2-acetylamino-3,3-diphenyl-propionic acid methyl [(2S)-1-({2-[(3S)-3-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}butyl]phenyl}amino)-1-oxo-3,3-diphenylpropan-2-yl]carbamate

合成工艺路线路线简述

    二苯基溴甲烷置于盐酸,六甲基磷酰三胺,Lithium Hydroxide,正丁基锂,四丁基溴化铵,Silica Gel,Lithium Bromide体系中,用 氯仿,乙腈 用作溶剂,化学反应 10.0H,反应生成L-3,3-二苯基丙氨酸
    参考文献:Design And Synthesis Of Side-Chain Conformationally Restricted Phenylalanines And Their Use For Structure-Activity Studies On Tachykinin Nk-1 Receptor
    标题:Design And Synthesis Of Side-Chain Conformationally Restricted Phenylalanines And Their Use For Structure-Activity Studies On Tachykinin Nk-1 Receptor
    摘要:Constrained Analogues Of Phenylalanine Have Been Conceptually Designed For Analyzing The Binding Pockets Of Phe(7) (S-7) And Phe(8) (S-8),Two Aromatic Residues Important For The Pharmacological Properties Of Sp,I.E.,L-Tetrahydroisoquinoleic Acid,L-Diphenylalanine,L-9-Fluorenylglycine (Flg),2-Indanylglycine,The Diastereomers Of L-1-Indanylglycine (Ing) And L-1-Benz[f]Indanylglycine (Bfi),And The Z And E Isomers Of Dehydrophenylalanine (Delta(Z)Phe,Delta(E)Phe). Binding Studies Were Performed With Appropriate Ligands And Tissue Preparations Allowing The Discrimination Of The Three Tachykinin Binding Sites,Nk-1,Nk-2,And Nk-3. The Potencies Of These Agonists Were Evaluated In The Guinea Pig Ileum Bioassay. According To The Binding Data,We Can Conclude That The S-7 Subsite Is Small,Only The Gauche (-) Probe [(2S,3S)-Ing(7)]Sp Presents A High Affinity For Specific Nk-1 Binding Sites. Surprisingly,The [delta(E)Phe(7)]Sp Analogue,Which Projects The Aromatic Ring Toward The Trans Orientation,Is Over 40-Fold More Potent Than The Z Isomer,[delta(Z)Phe(7)]Sp. A Plausible Explanation Of These Conflictual Results Is That Either The Binding Protein Quenches The Minor Trans Rotamer Of [(2S,3S)-Ing(7)]Sp In Solution Or This Constrained Amino Acid Side Chain Rotates When Inserted In The Protein. In Position 8,The High Binding Affinities Of [flg(8)]Sp And [(2S,3S)-Bfi(8)]Sp Suggest That The S-8 Subsite Is Large Enough To Accept Two Aromatic Rings In The Gauche (-) And One Aromatic Ring In The Trans Direction. Peptides Bearing Two Conformational Probes In Positions 7,8,Or 9 Led To Postulate That S-7,S-8,And S-9 Subsites Are Independent From Each Other. The Volumes Available For Side Chains 7 And 8 Can Be Estimated To Be Close To 110 And 240 Angstrom(3),Respectively. The Large Volume Of The S-8 Subsite Raises Question On The Localization Of The Sp-Binding Site In The Nk-1 Receptor. If Sp Were To Bind In The Transmembrane Domains,The Cleft Defined By The Seven Transmembrane Segments Must Rearrange During The Binding Process In Order To Bind A Peptide In An Ac-Helical Structure And At Least One Large Binding Subsite In Position 8. Thus,Indirect Topographical Analysis With Constrained Amino Acids Might Contribute To The Analysis Of The Receptor/ligand Dynamics. Finally,This Study Demonstrates That A Good Knowledge Of The Peptidic Backbone Structure And A Combination Of Constrained Amino Acids Are Prerequisites To Confidently Attribute The Preferred Orientation(S) Of An Amino Acid Side Chain.
    Doi:10.1021/jm00037A009

    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-10087221-B2
    优先权日:2013-03-21
    标题 :Synthesis of hydantoin containing peptide products
    发明人:HENKEL BERND
    权利人:SANOFI AVENTIS DEUTSCHLAND
    摘要:The present invention relates to a method of synthesizing a peptide product comprising at least one hydantoin group. The peptide product may be used as a reference material for the quality control of pharmaceutical peptides, particularly for the quality control of exendin peptides. Further, the invention relates to hydantoin building blocks, a method for manufacturing such building blocks and their use for the synthesis of peptide products.

    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:WO-2008098280-A1
    优先权日:2007-02-16
    标题:Methods for the synthesis of dicarba bridges in growth hormone peptides
    发明人:ROBINSON ANDREA JANE; VAN LIEROP BIANCA; WHELAN AMANDA
    权利人:POLYCHIP PHARMACEUTICALS PTY; UNIV MONASH; ROBINSON ANDREA JANE; VAN LIEROP BIANCA; WHELAN AMANDA
    摘要:The invention relates to peptides comprising the carboxy terminal sequence of a growth hormone or an analogue of such a peptide in which the disulfide bridge is replaced by a dicarba bridge. Compositions containing such dicarba bridged peptides and method of treating obesity in an animal such as a human comprising administration of such dicarba bridged peptides are also disclosed.

    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.
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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):1793-1134.

    合成参考文献


    参考文献:10.1007/bf01388170
    摘要:Calmes M, Daunis J. How to build optically active alpha-amino acids. Amino Acids. 1999;16(3-4):215–50. doi: 10.1007/bf01388170.
    参考文献:10.1007/s00894-019-4080-x
    摘要:Bystrov VS, Zelenovskiy PS, Nuraeva AS, Kopyl S, Zhulyabina OA, Tverdislov VA. Molecular modeling and computational study of the chiral-dependent structures and properties of self-assembling diphenylalanine peptide nanotubes. Journal of Molecular Modeling. 2019 Jun 25;25(7):199. doi: 10.1007/s00894-019-4080-x.
    参考文献:10.1007/s13277-014-2563-z
    摘要:Zhao J, Xu H, He M, Wu Y. Glucocorticoid receptor DNA binding factor 1 expression and osteosarcoma prognosis. Tumour Biol. 2014 Dec;35(12):12449–58. doi: 10.1007/s13277-014-2563-z.
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