(S)-1-((S)-2-((benzyloxy)carbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride | 87297-14-1

• 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: (S)-1-((S)-2-((benzyloxy)carbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride
• 英文别名: L-phenylalanyl-L-proline benzyl ester hydrochloride；H-Phe-Pro-OBzl*HCl；HCl*Phe-Pro-OBzl；HCl*HPheProOBzl；H-Phe-Pro-OBzl hydrochloride；L-phenylalanyl-L-proline, benzyl ester, hydrochloride；L-phenylalanyl-L-proline benzylester hydrochloride；benzyl (2S)-1-[(2S)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carboxylate;hydrochloride
• CAS: 87297-14-1；96935-61-4
• 化学式: C₂₁H₂₄N₂O₃*ClH
• 分子量: 388.894
• InChiKey: VWVBMRYJHXTMMX-HLRBRJAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-((S)-2-((benzyloxy)carbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride 在 N-甲基吗啉 、 盐酸 、 palladium on activated charcoal 、 五氟苯基二苯基磷酸酯 、 氢气 、 N,N-二异丙基乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 31.14h， 生成 (6S,9S,12S,14aS,20S,23S,25aS)-20-benzyl-6,12-di((S)-sec-butyl)-9-(hydroxymethyl)-23-isobutylhexadecahydro-1H-dipyrrolo[1,2-a:1',2'-j][1,4,7,10,13,16,19]heptaazacyclohenicosine-5,8,11,14,19,22,25(25aH)heptaone
  参考文献：
  名称：

  合成Rolloamide B的改进途径

  摘要：

  已经描述了用于合成环状七肽Rolloamide B的高产率方法。引入有效的氯甲酸异丁酯（IBCF）介导的直接偶联反应，以改善向Rolloamide B的合成途径。此外，初步的生物测定表明其对革兰氏阴性细菌和真菌具有潜在的活性。

  DOI：

  10.1016/j.tetlet.2016.07.044
• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 盐酸 、 TEA 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 4.0h， 生成 (S)-1-((S)-2-((benzyloxy)carbonyl)pyrrolidin-1-yl)-1-oxo-3-phenylpropan-2-aminium chloride
  参考文献：
  名称：

  Kubik, Aleksandra; Szewczuk, Zbigniew; Siemion, Ignacy Z., Polish Journal of Chemistry, 1988, vol. 62, # 4-6, p. 457 - 464

  摘要：

  DOI：

文献信息

• Non-linear hydrophobic-induced pKa shifts: Implications for efficiency of conversion to chemical energy
  作者：Dan W. Urry、D. Channe Gowda、Shao Qing Peng、Timothy M. Parker

  DOI：10.1016/0009-2614(95)00442-7

  日期：1995.6

  Phe residues, a non-linear hydrophobic-induced pKa shift was observed with a ΔpKa of 0.4 (Asp) and 0.3 (Glu) on addition to 2 Phe residues per 30mer but with a ΔpKa of 4.7 (Asp) and 2.7 (Glu) on going from 4 Phe/30mer to 5 Phe/30mer. As a shift in pKa can be equivalent to the conversion to chemical energy from whatever energy input — mechanical, chemical, electrochemical, pressure or light — which effects

  通过在能够显示疏水折叠和组装过渡的聚三糖肽中每三十个残基使用一个Asp或一个Glu，并将五个Val残基中的一组（最接近Asp或Glu残基）逐步转变为疏水性更高的Phe残基，非线性疏水诱导的p ķ一个移位用观察到Δ p ķ一个上除了每30聚体，但用2个的Phe残基的0.4（ASP）和0.3（谷氨酸）Δ p ķ一个4.7（ASP）和2.7 （Glu）从4 Phe / 30mer升至5 Phe / 30mer。作为p K a的偏移可以等同于从任何能量输入（机械，化学，电化学，压力或光能）转化为化学能，这会影响疏水性的变化，非线性疏水诱导的p K a位移意味着能量转化的效率随着蛋白质基聚合物的疏水性。
• Hydrophobicity dependence of oxidation of tetrapeptides of elastin sequences with Mn(III): Synthesis, characterization, kinetics, and mechanistic study
  作者：B. K. Kempe Gowda、H. S. Prasad、K. S. Rangappa、D. Channe Gowda

  DOI：10.1002/kin.10015

  日期：2002.1

  The analogues of elastin sequences, glycyl-glycyl-alanyl-proline (GGAP), glycyl-glycyl-phenylalanyl-proline (GGFP), and glycyl-glycyl-isoleucyl-proline (GGIP) were synthesized by classical solution phase method and characterized. The kinetics of oxidation of these tetrapeptides (TETP) by Mn(III) has been studied in the presence of sulphate ions in acidic solution at 25°C. The reaction was followed

  弹性蛋白序列的类似物，甘氨酰-甘氨酰-丙氨酰-脯氨酸(GGAP)、甘氨酰-甘氨酰-苯丙氨酰-脯氨酸(GGFP)和甘氨酰-甘氨酰-异亮氨酰-脯氨酸(GGIP)通过经典液相法合成并表征。在 25°C 酸性溶液中存在硫酸根离子的情况下，研究了 Mn(III) 对这些四肽 (TETP) 的氧化动力学。在 λmax = 500 nm 处用分光光度法跟踪反应。观察到速率对 [Mn(III)] 和 [TETP] 的一级依赖性。该速率与还原产物、Mn(II) 和氢离子的浓度无关。研究了改变介质介电常数和添加阴离子（如硫酸盐、氯化物或高氯酸盐）的影响。激活参数已使用 Arrhenius 和 Erying 图进行了评估。氧化产物被分离和表征。提出了在限速步骤中涉及 TETP 与 Mn(III) 反应的机制。在这些序列的氧化速率和疏水性之间注意到明显的相关性，其中增加的疏水性导致增加的氧化速率。© 2001 John
• Dipeptide derivatives and antihypertensive drugs containing them
  申请人：Ajinomoto Co., Inc.

  公开号：US04971993A1

  公开（公告）日：1990-11-20

  There are disclosed dipeptide derivatives represented by the general formula: ##STR1## wherein R.sup.1 is a radical selected from the group consisting of alkyl, aralkyl and aryl groups optionally containing one or more substituent groups, R.sup.2 is a radical selected from the group consisting of hydrogen atoms and alkyl, aralkyl and aryl groups optionally containing one or more substituent groups, R.sup.3 is a radical selected from the group consisting of hydrogen atoms and alkyl, aralkyl and aryl groups optionally containing one or more substituent groups, R.sup.4 is a radical selected from the group consisting of hydrogen atoms and alkyl, aralkyl and aryl groups optionally containing one or more substituent groups, and R.sup.5 is a radical selected from the group consisting of hydroxyl, amino, hydroxyamino, alkyloxy, aralkyloxy, aryloxy, alkylamino, aralkylamino, arylamino, alkyloxyamino, aralkyloxyamino, aryloxyamino, acylamino and sulfonylamino groups, which alkyloxy, aralkyloxy and aryloxy groups optionally containing one or more substituent groups; wherein R.sup.3 may be combined with R.sup.2 or R.sup.4 to form an alkylene bridge optionally containing one or more oxygen atoms, sulfur atoms and nitrogen atoms and optionally containing one or more substituent groups. However, certain dipeptide derivatives within the above general formula are excluded from the invention. The dipeptide derivatives are useful for the treatment of hypertension.

  本发明公开了一种二肽衍生物，其通式为：##STR1## 其中，R.sup.1是从烷基，芳基烷基和芳基组成的基团中选择的基团，可选地含有一个或多个取代基团；R.sup.2是从氢原子和烷基，芳基烷基和芳基组成的基团中选择的基团，可选地含有一个或多个取代基团；R.sup.3是从氢原子和烷基，芳基烷基和芳基组成的基团中选择的基团，可选地含有一个或多个取代基团；R.sup.4是从氢原子和烷基，芳基烷基和芳基组成的基团中选择的基团，可选地含有一个或多个取代基团；R.sup.5是从羟基，氨基，羟氨基，烷氧基，芳基烷氧基，芳氧基，烷基氨基，芳基烷基氨基，芳基氨基，烷氧基氨基，芳基烷氧基氨基，芳氧基氨基，酰基氨基和磺酰基氨基组成的基团中选择的基团，其中，烷氧基，芳基烷氧基和芳氧基基团可选地含有一个或多个取代基团；其中，R.sup.3可以与R.sup.2或R.sup.4结合形成一个烷基桥，可选地含有一个或多个氧原子，硫原子和氮原子，并可选地含有一个或多个取代基团。然而，上述通式中的某些二肽衍生物被排除在本发明之外。这些二肽衍生物对高血压的治疗有用。
• Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials – A novel approach to enhance biocompatibility
  作者：R. Suhas、S. Chandrashekar、D. Channe Gowda

  DOI：10.1016/j.ejmech.2010.12.005

  日期：2011.2

  The peptides of elastin sequences chosen for the present study included tetrapeptides, pentapeptides and tricosapeptides (30 amino acids), synthesized by classical solution phase method and conjugated to [3-(4-piperidyl)-6-fluoro-1,2-benzisoxazole]. The structures of the compounds were confirmed by physical and spectroscopic techniques followed by the antimicrobial evaluation by both agar well diffusion and microdilution methods. Here we wish to report the effect of conjugation of these moieties which enabled us to identify a novel set of peptides conjugated to heterocycle which have exhibited more potent antimicrobial activity than the conventional drugs used. Further, conjugates of tricosamers 34 and 35 were able to inhibit the growth of fungal species at 3-5 mu g/mL which is nearly 5 fold more potent than the reference drug. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Structure-Based Rationale Design and Synthesis of Aurantiamide Acetate Analogues - Towards a New Class of Potent Analgesic and Anti-inflammatory Agents
  作者：Ramesh Suhas、Dase Channe Gowda

  DOI：10.1111/j.1747-0285.2012.01331.x

  日期：2012.5

  A series of new aurantiamide acetate analogues were synthesized by modifying its N‐terminal substitution and the amino acid residue. The structure of all these compounds was established on the basis of analytical and spectral studies. All the new derivatives were evaluated in vivo for their analgesic activity by tail flick method in mice and anti‐inflammatory activity against carrageenan‐induced oedema in albino rats at different doses (25, 50 and 100 mg/kg body weight). All the compounds exhibited significant pharmacological activity with no ulcerogenic liability. In particular, pentapeptides and tricosamers (30 amino acids) containing analogues have demonstrated high potency than the reference standards. These compounds hold promise for further development.