α-amino-cis-4-hexenoic acid | 19458-75-4

• 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: α-amino-cis-4-hexenoic acid
• 英文别名: (Z)-2-aminohex-4-enoic acid；cis-2-amino-4-hexenoic acid；DL-2-Amino-cis-hexen-(4)-saeure；DL-2-Amino-cis-4-hexensaeure；2-Amino-cis-4-hexenoic acid
• CAS: 19458-75-4
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: OPOBBDXDRHKTJF-IHWYPQMZSA-N

物化性质

• 沸点：
  239.3±33.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-amino-cis-4-hexenoic acid 在 乙酸酐 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-formyl-cis-crotylglycine phenyl ester
  参考文献：
  名称：

  Remote Binding Energy in Antibody Catalysis:  Studies of a Catalytically Unoptimized Specificity Pocket

  摘要：

  Binding interactions remote from the hydrolytic reaction center have been probed with substrate and phosphonate transition state analogues to understand how these types of interactions are used to promote catalysis in the 17E8 system, We find that the hapten-generated recogniton pocket in 17E8 has properties that are analogous to those of specificity pockets in enzymes, pie have also found that there are specific requirements to form catalytically productive interactions between the side chain and the recognition pocket including conformation, size, and geometry. An additional requirement includes Favorable simultaneous interactions between the side chain and binding packet along with favorable interactions with the oxyanion hole. The 17E8 side chain recognition pocket seems to be less catalytically efficient than analogous pockets in enzymatic systems. The apparent binding energy gained from the methylene-packet interactions in the 17E8 system is significantly smaller than those observed in natural enzymes. Furthermore, 17E8 does not use specific interactions in the recognition pocket to significantly affect catalytic turnover (k(cat)) which is thought to be a trait of an unoptimized catalyst. Analysis of the crystal structure of the 17E8,hapten complex has allowed for the identification of differences between the active sites of 17E8; and several proteases, The identified differences give insight to the sources of the inefficient use of binding energy.

  DOI：

  10.1021/ja983017e
• 作为产物：
  描述：

  (Z)-2-Acetylamino-hex-4-enoic acid ethyl ester 生成 α-amino-cis-4-hexenoic acid
  参考文献：
  名称：

  通过非天然氨基酸体内掺入的蛋白质工程：通过蛋氨酸-tRNA合成酶控制蛋氨酸类似物的掺入

  摘要：

  将非天然氨基酸掺入是将新的化学和物理性质工程化为天然和人工蛋白质的重要​​策略。体内氨基酸向蛋白质中的掺入在很大程度上受氨酰基-tRNA合成酶（AARS）的控制。我们已经测量了通过甲硫基-tRNA合成酶（MetRS）通过ATP-PP i交换反应体外激活一组甲硫氨酸类似物的动力学常数。蛋氨酸类似物的体外活化与这些类似物在体内支持蛋白质合成的能力密切相关，从而证实了AARS在控制将非天然氨基酸掺入蛋白质中的关键作用。k cat / K m的蛋氨酸类似物该值比蛋氨酸的值低2000倍，可以支持在蛋白质表达的标准条件下合成典型目标蛋白质（mDHFR）。动力学常数与从常规细菌表达宿主观察到的蛋白质产量密切相关，表明宿主的MetRS活性可以在某些条件下控制蛋白质合成的水平。此外，增加细菌宿主的MetRS活性会导致补充蛋氨酸类似物高烯丙基甘氨酸和正亮氨酸的培养基中蛋白质的合成增加。这些结果表明了通过操纵细

  DOI：

  10.1016/s0040-4020(00)00833-4

文献信息

• [EN] MULTIFUNCTIONAL MEMBRANE-ACTIVE AMINOGLYCOSIDE-PEPTIDE CONJUGATES<br/>[FR] CONJUGUÉS AMINOGLYCOSIDE-PEPTIDE MULTIFONCTIONNELS À ACTIVITÉ MEMBRANAIRE
  申请人：UNIV CALIFORNIA

  公开号：WO2016025627A1

  公开（公告）日：2016-02-18

  Compositions and methods are disclosed that relate to aminoglycoside-linker-peptide (P-L-A) conjugates having unexpectedly advantageous dual-function bactericidal properties. Encompassed compounds are shown to be capable of energy independent bacterial plasma membrane disruption and to exhibit potent toxicity to bacteria including antibiotic-resistant bacteria. These and related embodiments will find uses for treating bacterial infections including overcoming antibiotic resistance.

  揭示了与氨基糖苷-连接肽（P-L-A）共轭物相关的具有意外优势双重杀菌性能的组合物和方法。所涵盖的化合物被证明能够独立于能量的细菌质膜破坏，并对包括抗生素耐药细菌在内的细菌表现出强大的毒性。这些及相关实施例将用于治疗细菌感染，包括克服抗生素耐药性。
• Efficient Incorporation of Unsaturated Methionine Analogues into Proteins in Vivo
  作者：Jan C. M. van Hest、Kristi L. Kiick、David A. Tirrell

  DOI：10.1021/ja992749j

  日期：2000.2.1

  translational activity. The terminally unsaturated compounds 2 and 3, however, proved to be excellent methionine surrogates: ^1H NMR spectroscopy, amino acid analysis, and N-terminal sequencing indicated ∼85% substitution of methionine by 2, while 3 showed 90−100% replacement. Both analogues also function efficiently in the initiation step of protein synthesis, as shown by their near-quantitative occupancy

  在大肠杆菌中测定了一组八种甲硫氨酸类似物的翻译活性。市售的正缬氨酸和正亮氨酸与 2-氨基-5-己烯酸 (2)、2-氨基-5-己烯酸 (3)、顺式-2-氨基-4-己烯酸 (4) 一起测定、反式-2-氨基-4-己烯酸（5）、6,6,6-三氟-2-氨基己酸（6）和2-氨基庚酸（7），均由乙酰氨基丙二酸二乙酯烷基化制备用适当的甲苯磺酸盐，然后水解。用质粒 pREP4 和 pQE15 转化的大肠杆菌甲硫氨酸营养缺陷型 CAG18491 作为表达宿主，通过测定类似物在不存在的情况下支持测试蛋白质二氢叶酸还原酶 (DHFR) 合成的能力来测定翻译活性添加的蛋氨酸。与正亮氨酸 (9) 相比，正缬氨酸 (8) 和 7 均不显示翻译活性，这说明了氨基酸侧链长度的重要性，正亮氨酸 (9) 在测定条件下支持蛋白质合成。4 和 5 的内部烯烃功能阻止这些类似物掺入测试蛋白质中，氟化类似物 6 没有产生翻译活性的证据。然而，末端不饱和化合物
• Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine
  作者：Masaharu Sugiura、Chieko Mori、Keiichi Hirano、Shū Kobayashi

  DOI：10.1139/v05-096

  日期：2005.6.1

  Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments have suggested that the isomerization took place via 2-aza (or azonia) Cope rearrangement of imines derived from γ-adducts and glyoxylic acid.Key words: hydroxyglycine, glyoxylic acid, allylboronates, α-amino acids, allylglycines, isoleucine, alloisoleucine, stereoselective reactions, isomerization, 2-aza (azonia) Cope rearrangement.

  羟基甘氨酸，即乙酰乙酸的氨加合物，在三乙胺存在下与甲醇中的各种烯基硼酸酯反应，可直接高立体选择性地得到未保护的α-氨基酸。例如，与(E)-和(Z)-丙烯基硼酸酯的反应分别得到相应的反式和顺式丙烯基化产物（氢化后为异亮氨酸和异亮氨酸）具有高对映选择性。有趣的是，在某些情况下，在反应条件下发现产物的异构化（从γ-加合物到α-加合物）。对照实验表明，异构化是通过从γ-加合物和乙二醛酸衍生的亚胺的2-氮杂Cope重排反应发生的。关键词：羟基甘氨酸，乙二醛酸，烯基硼酸酯，α-氨基酸，烯基甘氨酸，异亮氨酸，异亮氨酸，立体选择性反应，异构化，2-氮杂Cope重排。
• Overexpression of aminoacyl-tRNA synthetases for efficient production of engineered proteins containing amino acid analogues
  申请人：——

  公开号：US20020042097A1

  公开（公告）日：2002-04-11

  Methods for producing modified polypeptides containing amino acid analogues are disclosed. The invention further provides purified dihydrofolate reductase polypeptides, produced by the methods of the invention, in which the methionine residues have been replaced with homoallyglycine, homoproparglycine, norvaline, norleucine, cis-crotylglycine, trans-crotylglycine, 2-aminoheptanoic acid, 2-butynylglycine and allylglycine.

  本发明揭示了制备含有氨基酸类似物的修饰多肽的方法。本发明进一步提供了通过本发明的方法生产的纯化的二氢叶酸还原酶多肽，其中甲硫氨酸残基已被替换为同烯基甘氨酸、同丙炔基甘氨酸、正异戊氨酸、正异癸氨酸、顺-十四烷基甘氨酸、反-十四烷基甘氨酸、2-氨基庚酸、2-丁炔基甘氨酸和烯丙基甘氨酸。
• OVEREXPRESSION OF AMINOACYL-tRNA SYNTHETASES FOR EFFICIENT PRODUCTION OF ENGINEERED PROTEINS CONTAINING AMINO ACID ANALOGUES
  申请人：Tirrell David A.

  公开号：US20080160609A1

  公开（公告）日：2008-07-03

  Methods for producing modified polypeptides containing amino acid analogues are disclosed. The invention further provides purified dihydrofolate reductase polypeptides, produced by the methods of the invention, in which the methionine residues have been replaced with homoallylglycine, homoproparglycine, norvaline, norleucine, cis-crotylglycine, trans-crotylglycine, 2-aminoheptanoic acid, 2-butynylglycine and allylglycine.

  本发明揭示了一种生产含有氨基酸类似物的改性多肽的方法。本发明进一步提供了经本发明方法生产的纯化的脱氢叶酸还原酶多肽，其中甲硫氨酸残基已被替换为同丙烯基甘氨酸，同丙炔基甘氨酸，正戊氨酸，正亮氨酸，顺-十四烯基甘氨酸，反-十四烯基甘氨酸，2-氨基庚酸，2-丁炔基甘氨酸和丙烯基甘氨酸。