(R)-(-)-4-Amino-5-phenylvaleriansaeure | 63328-06-3

• 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: (R)-(-)-4-Amino-5-phenylvaleriansaeure
• 英文别名: (4r)-4-Amino-5-phenylpentanoic acid
• CAS: 63328-06-3
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: URBAOHLJWLYLQE-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(-)-4-Amino-5-phenylvaleriansaeure 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (4R)-4-amino-5-phenylpentan-1-ol
  参考文献：
  名称：

  A Versatile Annulation Protocol toward Novel Constrained Phosphinic Peptidomimetics

  摘要：

  [GRAPHICS]The development of a novel 3-center 2-component annulation reaction between alpha,omega-carbamoylaldehydes and suitably monoalkylated phosphinic acids is reported. Depending on the starting alpha,omega-carbamoylaldehyde, diverse phosphinic scaffolds varying in the size of their rigidity element, the nature and stereochernistry of substituents, and the participation of heteroatoms in the azacyclic ring system can be obtained in one synthetic step and in high yield. In addition, this methodology allows the synthesis of Fmoc-protected constrained aminophosphinic acids that can be easily converted to suitable pseudodipeptide building blocks compatible with the requirements of peptide synthesis on the solid phase. Finally, the careful choice of both substituents and protecting groups can provide functionally diverse, orthogonally protected constrained scaffolds for extended derivatization of the target phosphinic peptidomimetic structrures.

  DOI：

  10.1021/jo071081l
• 作为产物：
  描述：

  (S)-3-benzyloxycarbonylamino-4-phenylbutyric acid 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 silver benzoate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-(-)-4-Amino-5-phenylvaleriansaeure
  参考文献：
  名称：

  Beitrag zur不对称性在Katalyse mit optisch aktivenAminosäuren上合成自行车。合成von（S）-2-吡咯烷基丙酸酯和（R）-4-氨基-5-苯基缬草†

  摘要：

  光学活性氨基酸催化双环化合物的不对称合成。（S）-2-吡咯烷丙酸和（R）-4-氨基-5-苯基戊酸的合成

  DOI：

  10.1002/hlca.19770600826

文献信息

• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：POLYPHOR AG

  公开号：US20150051183A1

  公开（公告）日：2015-02-19

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义的大环环系统由三个不同的分子部分组成：模板A、构象调节剂B和桥C。由这种环系统I描述的大环可通过并行合成或溶液中或固相上的组合化学轻松制造。它们被设计用于与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，酶的抑制活性或抗菌活性。特别是，这些大环显示对亚型1的内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶卡特普辛S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃素3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Potent Antimicrobial Activity of Lipidated Short α,γ-Hybrid Peptides
  作者：Sushil N. Benke、Hirekodathakallu V. Thulasiram、Hosahudya N. Gopi

  DOI：10.1002/cmdc.201700370

  日期：2017.10.9

  Herein we report the potent antimicrobial activity of α,γ‐hybrid lipopeptides composed of 1:1 alternating α‐ and γ‐amino acids. Along with their potent antimicrobial activity against various Gram‐positive and Gram‐negative bacteria, these hybrid lipopeptides were found to be less hemolytic. Studies into the mechanism of action revealed that these short cationic lipopeptides bind and disrupt the bacterial

  本文中，我们报告了由1：1交替的α-和γ-氨基酸组成的α，γ-混合脂肽的有效抗菌活性。这些杂合脂肽除了具有针对各种革兰氏阳性和革兰氏阴性细菌的强效抗菌活性外，还具有较小的溶血作用。对作用机理的研究表明，这些短阳离子脂肽结合并破坏细菌细胞膜。时间杀灭动力学分析表明，有效的α，γ-混合脂肽可在不到20分钟的时间内完全抑制细菌生长。总体而言，这些α，γ-混合脂肽显示出令人鼓舞的抗菌活性以及较低的溶血活性，使其非常适合进一步探索有效的脂肽抗生素的设计。
• [EN] THIOPHENE AMINO ACID DERIVATIVES, PROCESS FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES D'ACIDE AMINE THIOPHENIQUE, LEUR PROCEDE DE PREPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：WARNER LAMBERT CO

  公开号：WO2005003115A1

  公开（公告）日：2005-01-13

  Compounds of formula (I), in which: R1 and R2, which may be identical or different, independently of each other, each represent a group selected from: hydrogen, halogen, cyano, nitro, halo(C1-C6)alkyl, halo(C1-C6)alkoxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, -OR4, -NR4R5, -S(O)nR4, -C(O)R4, -CO2R4, -O-C(O)R4, -C(O)NR4R5, -NR5-C(O)R4, -NR5-SO2R4, -T-CN, -T-OR4, -T-OCF3, -T-NR4R5, -T-S(O)nR4, -T-C(O)R4, -T-CO2 R4, -T-O-C(O)R4, -T-C(O)NR4 R5, -T-NR5-C(O)R4, -T-NR5-SO2R4, -R6 and -T-R6 in which n, T, R4, R5 and R6 are as defined in the description ; m represents an integer between 0 and 4 inclusive ; p represents an integer between 0 and 4 inclusive ; q represents an integer between 0 and 4 inclusive ; R7 represents a group selected from aryl, cycloalkyl and a heterocycle, each of these groups being optionally substituted; R8 represents a group selected from carboxyl, (C1-C6)alkoxycarbonyl, (C1-C7)acyl, hydroxy(C1-C6)alkylcarbonyl, (C1-C6)alkoxy(C1-C6)alkylcarbonyl, tetrazole, amino, aminocarbonyl and amino(C1-C6)alkylcarbonyl; the isomers thereof and the addition salts thereof with a pharmaceutically acceptable acid or base, and the pharmaceutical compositions which are useful for treating pathologies associated with an inhibition of metalloproteases.

  化合物的化学式（I）中：R1和R2可以相同也可以不同，分别表示从以下选定的基团中选择的基团：氢、卤素、氰基、硝基、卤代（C1-C6）烷基、卤代（C1-C6）氧基、（C1-C6）烷基、（C2-C6）烯基、（C2-C6）炔基、-OR4、-NR4R5、-S（O）nR4、-C（O）R4、-CO2R4、-O-C（O）R4、-C（O）NR4R5、-NR5-C（O）R4、-NR5-SO2R4、-T-CN、-T-OR4、-T-OCF3、-T-NR4R5、-T-S（O）nR4、-T-C（O）R4、-T-CO2 R4、-T-O-C（O）R4、-T-C（O）NR4 R5、-T-NR5-C（O）R4、-T-NR5-SO2R4、-R6和-T-R6其中n、T、R4、R5和R6如描述中所定义；m表示0到4之间的整数；p表示0到4之间的整数；q表示0到4之间的整数；R7表示从芳基、环烷基和杂环中选择的基团，这些基团可以选择性地被取代；R8表示从羧基、（C1-C6）烷氧羰基、（C1-C7）酰基、羟基（C1-C6）烷基羰基、（C1-C6）烷氧基（C1-C6）烷基羰基、四唑基、氨基、氨基羰基和氨基（C1-C6）烷基羰基中选定的基团；其异构体及其与药用酸或碱形成的可接受的加合盐，以及用于治疗与金属蛋白酶抑制相关的病理的药物组合物。
• [EN] PIPECOLIC LINKER AND ITS USE FOR CHEMISTRY ON SOLID SUPPORT<br/>[FR] LIEUR PIPÉCOLIQUE ET SON UTILISATION POUR UNE CHIMIE SUR SUPPORT SOLIDE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2010023295A1

  公开（公告）日：2010-03-04

  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.

  本发明涉及一种吡啶哌酸链连接剂及其在有机合成中作为固相连接剂的用途。所述吡啶哌酸固相连接剂可用于将功能基团偶联在一起，这些功能基团可选择为一级胺、二级胺、芳香胺、醇、酚和硫醇。特别地，所述吡啶哌酸固相连接剂可用于肽或伪肽合成，例如反向N到C肽合成或反向逆转肽合成，或用于小有机分子的合成。