L-亮氨酰-L-缬氨酸 | 13588-95-9

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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
• 中文名称: L-亮氨酰-L-缬氨酸
• 英文名称: L-leucyl-L-valine
• 英文别名: Leu-Val；(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-methylbutanoic acid
• CAS: 13588-95-9
• 化学式: C₁₁H₂₂N₂O₃
• 分子量: 230.307
• InChiKey: MDSUKZSLOATHMH-IUCAKERBSA-N

物化性质

• 熔点：
  >174° (dec.)
• 沸点：
  421.9±30.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)
• 溶解度：
  超声处理轻微溶于甲醇、超声处理少量溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  96.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  L-亮氨酰-L-缬氨酸 生成 cyclo-Leu-Val
  参考文献：
  名称：

  Cyclization of L-Leucyl-L-valine Dipeptide in the Crystal Phase under Non-Isоthermal Conditions

  摘要：

  DOI：

  10.1134/s1070363223110063
• 作为产物：
  描述：

  N-(N-((苄氧基)羰基)-L-亮氨酰)-L-缬氨酸 在 甲醇 、 钯 、 溶剂黄146 作用下， 生成 L-亮氨酰-L-缬氨酸
  参考文献：
  名称：

  Smith et al., Journal of Biological Chemistry, 1952, vol. 199, p. 801,808

  摘要：

  DOI：

文献信息

• Peptide Synthesis in Aqueous Solution. IV. Preparation and Properties of [<i>p</i>-(Benzyloxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Z-ODSP), [<i>p</i>-(<i>t</i>-Butoxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Boc-ODSP) and [<i>p</i>-(9-Fluorenylmethyloxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Fmoc-ODSP) as Water-Soluble<i>N</i>-Acylating Reagents
  作者：Ikunori Azuse、Masahiro Tamura、Keisuke Kinomura、Hideo Okai、Katsushige Kouge、Fumio Hamatsu、Tatsuya Koizumi

  DOI：10.1246/bcsj.62.3103

  日期：1989.10

  order to increase the applications of the water-soluble active ester method, water-soluble acylating reagents, [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate and [p-(9-fluorenylmethyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, were synthesized from of p-hydroxyphenyldimethylsulfonium methyl sulfate. These

  为了增加水溶性活性酯法的应用，水溶性酰化试剂[对(苄氧基羰基氧基)苯基]二甲基硫酸锍、[对(叔丁氧基羰氧基)苯基]二甲基硫酸锍和[对- (9-芴基甲氧基羰基氧基)苯基]二甲基锍甲基硫酸盐由对羟基苯基二甲基锍甲基硫酸盐合成。这些化合物在水中具有高溶解度（超过 30%），并且被发现可作为优异的水溶性酰化试剂，用于在水溶液中合成 N-苄氧羰基、N-叔丁氧羰基、N-9-芴基甲氧羰基氨基酸衍生物。他们在水性介质和氨基酸中将二肽转化为 N-酰基二肽。此外，还发现它们是保护赖氨酸、鸟氨酸、
• Examination of Structural Changes of Polymeric Amino Acid-Based Surfactants on Enantioselectivity:  Effect of Amino Acid Order, Steric Factors, and Number and Position of Chiral Centers
  作者：Eugene Billiot、Isiah M. Warner

  DOI：10.1021/ac9908804

  日期：2000.4.1

  In this study, a large number of polymeric chiral surfactants were examined and their performances in terms of enantiomeric resolution compared for a variety of chiral analytes. The surfactants investigated in this study include all possible dipeptide combinations of the l-form of alanine, valine, leucine, and the achiral amino acid glycine (except glycine-glycine). Also included in this study were the single amino acid surfactants of alanine, valine, and leucine as well as the single chiral center dipeptide surfactant poly(sodium undecyl-l-leucine-β-alanine) (poly l-SULβA). Several different aspects of polymeric dipeptide surfactants, as they pertain to chiral separations, are examined. Some of the factors investigated in this report include the effect of position and number of chiral centers, amino acid order, and steric effects.

  在本研究中，考察了大量聚合物手性表面活性剂，并比较了它们在多种手性分析物中对映体分辨性能的表现。本研究所调查的表面活性剂包括了所有可能的l-型丙氨酸、缬氨酸、亮氨酸以及非手性氨基酸甘氨酸（甘氨酸-甘氨酸除外）的二肽组合。研究中还包括了单一氨基酸表面活性剂的丙氨酸、缬氨酸和亮氨酸，以及具有单一手性中心的二肽表面活性剂聚（十一烷基-l-亮氨酸-β-丙氨酸钠）（聚l-SULβA）。本研究审查了与手性分离相关的聚二肽表面活性剂的几个不同方面。报告中调查的一些因素包括手性中心位置和数量的效应、氨基酸顺序及立体效应。
• Chiral Separations Using Dipeptide Polymerized Surfactants:  Effect of Amino Acid Order
  作者：Eugene Billiot、Javier Macossay、Stefan Thibodeaux、Shahab A. Shamsi、Isiah M. Warner

  DOI：10.1021/ac9709561

  日期：1998.4.1

  Chiral separations using various polymerized dipeptide surfactants in electrokinetic capillary chromatography (EKC) are investigated. The two main dipeptide surfactants used in this study were sodium N-undecylenyl-l-valine-l-leucine (l-SUVL), and sodium N-undecylenyl-l-leucine-l-valine (l-SULV). These studies were performed in order to determine if the order of amino acids in dipeptide surfactants is important in terms of chiral recognition and separations. Both the monomer and the polymer of these two surfactants were compared for the separation of two model atropisomers, (±)-1,1‘-bi-2-naphthol (BOH) and (±)-1,1‘-bi-2-naphthyl-2,2‘-diyl hydrogen phosphate (BNP). Some advantages and disadvantages of the polymer relative to the monomer are discussed. Four other surfactants, the polymers of sodium N-undecylenyl-l-leucine-l-leucine (l-SULL), sodium N-undecylenyl-l-valine-l-valine (l-SUVV), sodium N-undecylenyl-l-valine (l-SUV), and sodium N-undecylenyl-l-leucine (l-SUL), were also used in this study, and their performance was compared to that of poly(l-SULV). These data show conclusively that the order of amino acids in dipeptide surfactants has a dramatic effect on chiral recognition. Our investigations indicate that poly(l-SULV) provides the best enantioselectivity among the four dipeptide and two single amino acid surfactants for the separation of BNP and BOH. The advantages of poly(l-SULV) are demonstrated via the ultrafast separation of the enantiomers of BNP and BOH in less than 1 min.

  使用电动力学毛细管色谱法(EKC)研究了各种聚二肽表面活性剂的手性分离。本研究中使用的两种主要二肽表面活性剂是钠N-十一烯基-L-缬氨酸-L-亮氨酸(L-SUVL)和钠N-十一烯基-L-亮氨酸-L-缬氨酸(L-SULV)。这些研究的目的是确定二肽表面活性剂中氨基酸的顺序是否在手性识别和分离方面起着重要作用。比较了这两种表面活性剂的单体和聚合物，用于分离两个模型旋转异构体，即(±)-1,1'-双-2-萘酚(BOH)和(±)-1,1'-双-2-萘基-2,2'-二基磷酸氢(BNP)。讨论了聚合物相对于单体的一些优点和缺点。本研究还使用了其他四种表面活性剂，即钠N-十一烯基-L-亮氨酸-L-亮氨酸(L-SULL)、钠N-十一烯基-L-缬氨酸-L-缬氨酸(L-SUVV)、钠N-十一烯基-L-缬氨酸(L-SUV)和钠N-十一烯基-L-亮氨酸(L-SUL)的聚合物，并将其性能与聚(L-SULV)进行了比较。这些数据显示，二肽表面活性剂中氨基酸的顺序对手性识别有显著影响。我们的研究表明，在四种二肽和两种单氨基酸表面活性剂中，聚(L-SULV)在分离BNP和BOH方面提供了最佳的对映选择性。通过在不到1分钟的时间内超快分离BNP和BOH的对映体，展示了聚(L-SULV)的优势。
• Synthesis and antimicrobial activity of <i>α</i> -aminoboronic-containing peptidomimetics
  作者：Olga V. Gozhina、John Sigurd Svendsen、Tore Lejon

  DOI：10.1002/psc.2583

  日期：2014.1

  tripeptidomimetics containing an α‐amino boronic acid or boronate has been synthesized, and the activity toward Mycobacterium tuberculosis, Candida albicans, Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli and Pseudomonas aeruginosa has been screened. Although there is no clear structure–activity relationship, several compounds exhibit promising activity against different pathogens. Copyright

  已合成了175个包含α-氨基硼酸或硼酸酯的二肽模拟物和三肽模拟物的文库，并筛选了其对结核分枝杆菌，白色念珠菌，金黄色葡萄球菌，化脓性链球菌，大肠杆菌和铜绿假单胞菌的活性。尽管没有明确的构效关系，但几种化合物对不同病原体表现出有希望的活性。版权所有©2013欧洲多肽协会和John Wiley＆Sons，Ltd.
• The Steric Hindrance of the Stepwise Reaction of<i>N</i>-Carboxy α-Amino Acid Anhydride with the α-Amino Acid Ester
  作者：Masanao Oya、Tomoko Takahashi

  DOI：10.1246/bcsj.54.2705

  日期：1981.9

  The mechanisms of the reactions of 4-alkyloxazolidinediones (1) (N-carboxy α-amino acid anhydrides(NCAs)) with α-amino acid benzyl ester p-toluenesulfonates (2) were investigated in acetonitrile containing triethylamine at low and room temperatures. Two types of reactions were observed: (1) the polymerization of NCAs was initiated with a small amount of 2 to produce polypeptides (6), and (2) the dipeptide

  研究了 4-烷基恶唑烷二酮 (1) (N-羧基 α-氨基酸酐 (NCAs)) 与 α-氨基酸苄酯对甲苯磺酸酯 (2) 在低温和室温下在含三乙胺的乙腈中的反应机理。观察到两种类型的反应：（1）NCAs 的聚合反应是用少量的 2 引发的，产生多肽（6），（2）二肽苄酯（4）是通过 NCAs 与酯类。聚合和二肽形成 (1+2) 似乎都是由酯的氨基对 NCA 的 C-5 碳的亲核攻击引发的。当氨基酸酯 (R2) 的侧链比 NCA (R1) 的侧链更大时，聚合进行。相反，

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