CAS: 136315-77-0; (1R,2R)-2-Aminocyclopentanecarboxylic Acid

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158414-44-9 137170-89-9 143679-80-5

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CAS号611-10-9 环戊酮-2-羧酸乙酯 | CAS号163877-11-0 (1R,2R)-ethyl 2... | CAS号245115-25-7 2-B°C-氨基环戊酸

-(R)-(+)-α-Methylbenzylamine置于盐酸,三氟乙酸体系中,化学反应 10.0H,反应生成(1R,2R)-(-)-2-氨基-1-环戊烷羧酸
参考文献:Probing A Molecular Model Of Taste Utilizing Peptidomimetic Stereoisomers Of 2-Aminocyclopentanecarboxylic Acid Methyl Ester
标题:Probing A Molecular Model Of Taste Utilizing Peptidomimetic Stereoisomers Of 2-Aminocyclopentanecarboxylic Acid Methyl Ester
摘要:On The Basis Of The Preferred Conformations Of L-Aspartyl Dipeptide Derivatives Containing Alpha-Amino Acids At The Second Position And Their Retro-Inverso Analogues Deduced By A Combination Of X-Ray Crystallography,H-1 NMR Spectroscopy,And Molecular Mechanics Calculations,We Have Proposed A Model Describing The Molecular Array Required For The Sweet Taste. The Conformation Of A Sweet Molecule Is Described As Possessing An "L Shape",With The Ah (Proton Donor) And B (Proton Acceptor) Zwitterionic Ring Of The Aspartyl Moiety Forming The Stem,And The Hydrophobic Group X Forming The Base Of The "L". Planarity Of The Molecule In The X And Y Dimensions Is Critical For Sweet Taste. Substantial Deviation From This Plane Into Negative Z Dimension Is Correlated With Bitter Taste While Other Deviations Lead To Tasteless Molecules. To Examine The Model,The Preferred Conformations For A Series Of L-Aspartyl Dipeptides Containing A 2-Aminocyclopentanecarboxylic Acid (2-Ac5C) Residue At The Second Position Were Calculated Using Molecular Mechanics. The Peptidomimetic 2-Ac5C Residue Is A Beta-Amino Acid With Two Chiral Centers,Resulting In Four Isomers [trans-(1S,2S)-2-Ac5C,Trans-(1R,2R)-2-Ac5C,Cis-(1R,2S)-2-Ac5C,And Cis-(1S,2R)-2-Ac5C]. Two Stereoisomers,L-Aspartyl-Trans-(1R,2R)-2-Aminocyclopentanecarboxylic Acid Methyl Ester [asp-Trans-(1R,2R)-2-Ac5C-Ome] And L-Aspartyl-Cis-(1S,2R)-2-Aminocyclopentanecarboxylic Acid Methyl Ester [asp-Cis-(1S,2R)-2-Ac5C-Ome],Prefer The L-Shape Conformations And Are Thus Predicted To Be Sweet. For L-Aspartyl-Trans-(1S,2S)-2-Aminocyclopentanecarboxylic Acid Methyl Ester [asp-Trans-(1S,2S)-2-Ac5C-Ome],The Methyl Ester Group Projects Behind The Stem Of The L Shape,Producing A Large Negative Z Component And Is Predicted To Exhibit A Bitter Taste. The Calculations Predict That L-Aspartyl-Cis-(1R,2S)-2-Aminocyclopentanecarboxylic Acid Methyl Ester [asp-Cis-(1R,2S)-2-Ac5C-Ome] Will Be Tasteless. In This Investigation,In Addition To The Calculations,We Report The Synthesis And Experimental Conformational Analysis Of The Four Stereoisomers Of Asp-2-Ac5C-Ome. The Absolute Configurations Of The 2-Ac5C Residues Were Assigned By X-Ray Diffraction Studies And By Correlating Optical Rotation And Enantiomeric Excess Values. These Studies Fully Confirm Our Configurational Assignments Of The Stereoisomers Of Asp-2-Ac5C-Ome. Thus,The Structure-Taste Relationships Observed For The New Class Of L-Aspartyl Taste Ligands Containing The 2-Ac5C Beta-Amino Acid Methyl Esters In The Second Position Agree With And Strengthen Our Model For The Sweet And Bitter Taste Responses.
Doi:10.1021/jo00023A033

专利信息

专利号:US-9206222-B2
优先权日:2009-06-29
标题:Solid phase peptide synthesis of peptide alcohols
发明人：CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN
权利人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN; CENTRE NAT RECH SCIENT
摘要:The present invention relates to the synthesis of depsipeptides on solid phase support. Said depsipeptides are then implicated in a solution phase O—N acyl shift enabling to obtain the corresponding peptide alcohols.

专利号:US-8546533-B2
优先权日:2008-08-29
标 题:Pipecolic linker and its use for chemistry on solid support
发明人：MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES
权利人:MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES; CENTRE NAT RECH SCIENT; UNIV MONTPELLIER 1; UNIV JAGELLONE; UNIV MONTPELLIER II
摘要:The present invention relates to a pipecolic linker and its use as a solid-phase linker in organic synthesis. Said pipecolic solid-phase linker may be used for coupling functional groups chosen between primary amines, secondary amines, aromatic amines, alcohols, phenols and thiols. In particular, said pipecolic solid-phase linker may be used for peptide or pseudopeptide synthesis, such as the reverse N to C peptide synthesis or the retro-inverso peptide synthesis, or for the synthesis of small organic molecules.

专利号:US-2023295613-A1
优先权日:2020-02-14
标 题:Long chain carbon and cyclic amino acids substrates for genetic code reprogramming
发明人：JEWETT MICHAEL C; LEE JOONGOO; MOORE JEFFREY S; SCHWARZ KEVIN J
权利人:UNIV NORTHWESTERN; UNIV ILLINOIS
摘要:Abstract: Disclosed are methods, systems, components, and compositions for synthesis of sequence defined polymers. The methods, systems, components, and compositions may be utilized for incorporating novel substrates that include non-standard amino acid monomers and non-amino acid monomers into sequence defined polymers. As disclosed herein, the novel substrates may be utilized for acylation of tRNA via flexizyme catalyzed reactions. The tRNAs thus acylated with the novel substrates may be utilized in synthesis platforms for incorporating the novel substrates into a sequence defined polymer.

专利号:WO-2011000848-A1
优先权日:2009-06-29
标题 :Solid phase peptide synthesis of peptide alcohols

专利号:US-11759496-B2
优先权日:2016-05-10
标题:Compounds and pharmaceutical use thereof in the treatment of cancer
发明人：SUSIN SANTOS A; KAROYAN PHILIPPE; MERLE-BERAL HÉLÈNE
权利人:KAROYAN PHILIPPE
摘要:The present invention relates to a compound or a pharmaceutical salt thereof comprising a hexapeptide sequence of formula (I), its method of synthesis and its use in anticancer therapy. The invention also relates to a pharmaceutical composition for use in the treatment of cancer comprising at least one soluble peptide according to the invention or at least one acid nucleic according to the invention or at least one expression vector according to the invention, or at least one host cell according to the invention and a pharmaceutically acceptable carrier.

专利号:WO-2007091110-A1
优先权日:2006-02-09
标 题 :Enzymatic resolution process for the preparation of cycli-c beta-amino acid and ester enatiomers
发明人：FORRO ENIKO; FUELOEP FERENC
权利人:UNIV SZEGEDI; FORRO ENIKO; FUELOEP FERENC
摘要:The invention relates to a process for the preparation of cyclic β-amino acid and ester enantiomers of general formula (I) wherein R is hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, aryl and heteroaryl, wherein each ring may optionally be condensed; A is alkylene or alkenylene, and one or more carbon atoms of each groups may optionally be replaced with one or more heteroatoms; Rl and R2 are hydrogen or halogen, =(O)n, optionally halogenated alkyl, alkylidene, alkoxy, optionally protected hydroxy, optionally protected amino, mono- or dialkylamino and optionally substituted phenyl, or Rl and R2 taken together with one or any two atoms of the ring to which they are attached, form a saturated, unsaturated or aromatic fused homo- or heterocyclic ring; n is 0, 1 or 2; * denotes a chiral carbon atom; and the salts thereof, comprising the steps of hydrolysing a mixture of cyclic β-amino ester enantiomers with a stereoselective hydrolytic enzyme, and separating the obtained acid enantiomer and the unreacted ester enantiomer. The invention provides an enzymatic resolution procedure for the preparation of enantiomers of both the cis- and trans-cyclic β-amino acids and esters useful for the synthesis ' of biologically active agents.