H-Orn(Z)-OBzl | 73995-50-3

• 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: H-Orn(Z)-OBzl
• 英文别名: benzyl (2S)-2-amino-5-(phenylmethoxycarbonylamino)pentanoate
• CAS: 73995-50-3
• 化学式: C₂₀H₂₄N₂O₄
• 分子量: 356.422
• InChiKey: UEWJMZFPUBXDNV-SFHVURJKSA-N

物化性质

• 沸点：
  526.7±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  H-Orn(Z)-OBzl 在 palladium on activated charcoal 氢气 、 碳酸氢钠 、 甲基磺酰氯 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 (2S)-5-amino-2-(2'-oxazetidin-1'-yl)pentanoic acid
  参考文献：
  名称：

  A substrate analogue study on clavaminic acid synthase: possible clues to the biosynthetic origin of proclavamic acid

  摘要：

  对(2S)-5-氨基-(2′-氧杂环丁基-1′-甲基)戊酸与克拉瓦敏酸合酶进行培育，得到(2S)-5-氨基-2-(2′-氧杂环丁基-1′-甲基)戊-3,4-烯酸作为主要产物，同时还得到少量的前克拉瓦敏酸；将氨基改为氨基脲基后，反应模式从去饱和偏向羟基化。

  DOI：

  10.1039/c39930000500
• 作为产物：
  描述：

  L-鸟氨酸 在 氯化亚砜 作用下， 反应 24.0h， 生成 H-Orn(Z)-OBzl
  参考文献：
  名称：

  可能参与克拉维酸生物合成的肽的合成

  摘要：

  摘要 通过将 3-羟基丙酸与 L-鸟氨酸和 3-羟基-DL-鸟氨酸偶联合成了两种肽，稍后进行测试以确定它们是否与克拉维酸的生物合成有关。

  DOI：

  10.1080/00397919108016757

文献信息

• Relationship between Structure and Papain Inhibitory Activity of Epoxysuccinyl Amino Acid Derivatives
  作者：Masaharu Tamai、Takashi Adachi、Kiyoshi Oguma、Shigeo Morimoto、Kazunori Hanada、Sadafumi Ohmura、Masahiro Ohzeki

  DOI：10.1080/00021369.1981.10864575

  日期：1981.3

  A number of amino acid derivatives of DL-Zra/w-epoxysuccinic acid, with a general formula of R1O-ES-AA-OR2 (ES, DL-trans-epoxysuccinyl group; AA, amino acid residue) were newly synthesized and used for the study of structure-activity relationships of papain inhibition. Branched-alkyl amino acids, such as Leu, He and Val, as AA and hydrogen or an alkyl group substituted with a phenyl or cycloalkyl group as R1 were desirable for activity, respectively. However, R2 or the optical activities of ES and AA not so much influenced on the activity.

  一些DL-Zra/w-环氧琥珀酸氨基酸衍生物被新合成并用于木瓜蛋白酶抑制的结构-活性关系研究。通式为R1O-ES-AA-OR2（ES，DL-反式环氧琥珀酰基团；AA，氨基酸残基）。AA为支链烷基氨基酸，如Leu、He和Val，R1为氢或被苯基或环烷基取代的烷基，这类衍生物具有较好的活性。但R2或ES和AA的光学活性对活性的影响不大。
• Studies on the biosynthesis of clavulanic acid. Part 5. Absolute stereochemistry of proclavaminic acid, the monocyclic biosynthetic precursor of clavulanic acid
  作者：Keith H. Baggaley、Stephen W. Elson、Neville H. Nicholson、John T. Sime

  DOI：10.1039/p19900001521

  日期：——

  carried out with enantiomerically pure threonine derivatives to confirm that the formation of the β-lactam moiety did not impair the integrity of the α- and β-chiral centres and that the enzymatic deacylation reaction was capable of resolving the α-centre of an α-amino-β-hydroxy acid. The enantiomeric purity of intermediates was determined using HPLC, 1H NMR spectroscopy utilising the chiral solvating reagents

  通过显示其构成为（2 S，3 R）-5-氨基-3-羟基-2-（2-氧杂氮杂环丁烷-1-基）戊酸的途径合成了普罗维胺酸（1）。合成材料的光谱性质与天然proclavaminic酸的光谱性质相同，并且与天然产物一样，其通过clavaminic acid合酶转化为clavaminic acid（2）。设计了3-羟基鸟氨酸衍生物的有效合成方法，该方法可分离非对映异构体并通过大肠杆菌的酰基转移酶[EC 3.5.1.11]拆分苏式化合物。。随后通过将受保护的3-羟基鸟氨酸迈克尔加到丙烯酸中，然后使用三苯基膦/二-2-吡啶基二硫化物进行闭环，来修饰β-内酰胺环。用对映体纯的苏氨酸衍生物进行模型反应，以确认β-内酰胺部分的形成不会损害α-和β-手性中心的完整性，并且酶促脱酰反应能够解析α-内酰胺基。 α-氨基-β-羟基酸。中间体的对映体纯度使用HPLC，使用手性溶剂化试剂（R）-和（S）-1-（9-蒽基）-2
• Alkanoyl L-carnitine amides with aminoacids and pharmaceutical compositions containing same, for promoting regeneration of the nervous tissue, inhibiting neuronal degeneration, enhancing the processes of learning and memory, and for the treatment of coma
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0514359A2

  公开（公告）日：1992-11-19

  Amides of alkanoyl L-carnitines of general formula (1). wherein R is a straight or branched alkanoyl group having from 2 to 8 carbon atoms selected from acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, hexanoyl, 1-methylbutyryl, t-butylacetyl, 2-ethylbutyryl, 3-methylvaleryl, 4-methylvaleryl, 2-ethylhexanoyl and 2-propylpentanoyl; R' is the monovalent residue of a naturally occurring aminoacid selected from: and X- is the anion of a pharmacologically acceptable acid are active in regenerating the nervous tissue, inhibiting neuronal degeneration, enhancing the processes of learning and memory and for the treatment of coma. Orally or parenterally administrable compositions in unit dosage form comprise between about 50 and about 500 mg of an amide of formula (1).

  通式(1)的烷酰基 L-肉碱的酰胺。 其中 R 是具有 2 至 8 个碳原子的直链或支链烷酰基，选自乙酰基、丙酰基、丁酰基、异丁酰基、戊酰基、异戊酰基、己酰基、1-甲基丁酰基、叔丁基乙酰基、2-乙基丁酰基、3-甲基戊酰基、4-甲基戊酰基、2-乙基己酰基和 2-丙基戊酰基； R'是选自以下天然氨基酸的单价残基 和 X- 是药理上可接受的酸的阴离子，具有再生神经组织、抑制神经元退化、增强学习和记忆过程以及治疗昏迷的活性。 口服或肠外给药的单位剂型组合物包括约 50 至约 500 毫克的式 (1) 酰胺。
• Product-substrate engineering by bacteria: Studies on clavaminate synthase, a trifunctional dioxygenase
  作者：Matthew D. Lloyd、Kirsten D. Merritt、Victor Lee、Timothy J. Sewell、Byeng Wha-Son、Jack E. Baldwin、Christopher J. Schofield、Steve W. Elson、Keith H. Baggaley、Neville H. Nicholson

  DOI：10.1016/s0040-4020(99)00547-5

  日期：1999.8

  Evidence is presented that clavaminate synthase (CS) catalyses three oxidative reactions in the clavulanic acid biosynthetic pathway. The first CS catalysed step (hydroxylation) is separated from the latter two (oxidative cyclisation and desaturation) by the action of a hydrolytic enzyme, proclavaminate amidinohydrolase, which modifies (or 'mutates') the sidechain of the product of the first reaction thereby converting it into a substrate for the second CS catalysed reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Enzymatic Synthesis of Monocyclic β-Lactams
  作者：Mark C Sleeman、Colin H MacKinnon、Kirsty S Hewitson∗、Christopher J Schofield

  DOI：10.1016/s0960-894x(01)00806-x

  日期：2002.2

  An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N-2-(2-carboxyethyl)-L-arginine was synthesised and found to be a substrate for the enzyme. The epimeric products were characterised by H-1 NMR and mass spectrometric analyses. The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.