N,N'-双[苄氧羰基]-L-鸟氨酸 | 2274-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N'-双[苄氧羰基]-L-鸟氨酸
• 英文名称: (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid
• 英文别名: (S)-2,5-bis(((benzyloxy)carbonyl)amino)pentanoic acid；N,N'-bis(benzyloxycarbonyl)-L-ornithine；(S)-N,N'-dibenzyloxycarbonylornithine；N-Cbz-L-ornithine(δ-Cbz)；N^α.N^δ-bis-benzyloxycarbonyl-L-ornithine；N^α.N^δ-Bis-benzyloxycarbonyl-L-ornithin；(2S)-2,5-bis(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 2274-58-0
• 化学式: C₂₁H₂₄N₂O₆
• mdl: MFCD00037821
• 分子量: 400.431
• InChiKey: VBENHRFIEOLOJJ-SFHVURJKSA-N

物化性质

• 沸点：
  653.3±55.0 °C(Predicted)
• 密度：
  1.258

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N,N'-双[苄氧羰基]-L-鸟氨酸 在 N-甲基吗啉 、 氯甲酸异丁酯 、 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.42h， 以52%的产率得到dibenzyl (5-hydroxypentane-1,4-diyl)-(S)-dicarbamate
  参考文献：
  名称：

  [EN] BACTERIAL EFFLUX PUMP INHIBITORS
  [FR] INHIBITEURS DE POMPE D'EFFLUX BACTÉRIEN

  摘要：

  本文披露了公式I的化合物及其盐。还披露了包含公式I化合物的组合物和使用公式I化合物的方法。

  公开号：

  WO2018165612A1
• 作为产物：
  描述：

  L-鸟氨酸 、 氯甲酸苄酯 生成 N,N'-双[苄氧羰基]-L-鸟氨酸
  参考文献：
  名称：

  Differentiation among the four diastereomers of benzyloxycarbonyl-protected γ-hydroxyornithine in negative-ion fast atom bombardment mass spectrometry

  摘要：

  AbstractDiscrimination among the four γ‐hydroxyornithine diastereomers was studied by fast atom bombardment mass spectrometry (FABMS). It is impossible to distinguish among the four diastereomers of this amino acid by positive‐ and negative‐ion FAB and collisionally activated dissociation MS, but benzyloxycarbonyl group protection of the α‐ and δ‐amino groups in γ‐hydroxyornithine allows differentiation among the diastereomers in negative‐ion FABMS. The negative‐ion mass spectra of benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers showed differences among the abundances of the molecule ion [M – H]‐, the dehydrated ion [M — H — H2O]‐ due to the loss of the γ‐hydroxyl group and the fragment ions formed from both [M — H]‐ and [M — H — H2O]‐ ions. On the other hand, no difference was found between the fragmentations of the benzyloxycarbonyl‐protected enantiomers of ornithine in negative‐ion FABMS. These results indicate that the orientation of the γ‐hydroxyl group and the existence of two benzene rings in the benzyloxycarbonyl group are important factors which are responsible for the fragmentations of the four benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers in negative‐ion FABMS. These studies also showed that the negative‐ion FABMS for benzyloxycarbonyl‐protected γ‐hydroxyornithine diastereomers is a useful method for determining the configuration of each diastereomer of γ‐hydroxyornithine.

  DOI：

  10.1002/oms.1210290509

文献信息

• Antibacterial amide macrocycles VII
  申请人：Endermann Rainer

  公开号：US20080306040A1

  公开（公告）日：2008-12-11

  The invention relates to antibacterial amide macrocycles and methods for their preparation, their use for the treatment and/or prophylaxis of diseases as well as their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially bacterial infections.

  这项发明涉及抗菌酰胺大环化合物及其制备方法，其用于治疗和/或预防疾病以及用于生产治疗和/或预防疾病的药物，特别是细菌感染的药物。
• [EN] CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO<br/>[FR] CONJUGUÉS COMPRENANT DES GROUPES PEPTIDIQUES ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：LEGOCHEM BIOSCIENCES INC

  公开号：WO2017089894A1

  公开（公告）日：2017-06-01

  In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

  在某些方面，本发明涉及一种抗体药物偶联物，包括：抗体；连接体；以及至少两个活性剂。在优选的实施例中，连接体包括由多个氨基酸组成的肽序列，其中至少两个活性剂通过共价键与氨基酸的侧链连接。抗体药物偶联物可以包括自焚基团，优选地是两个自焚基团。连接体可以包括O-取代的肟，例如，其中肟的氧原子被取代以与活性剂形成共价键连接；肟的碳原子被取代以与抗体形成共价键连接。
• A One-Pot Peptide Synthesis via<u>Se</u>-phenyl Carboselenoate in Mixed Aqueous/Organic Solvent System
  作者：Sunil Kumar Ghosh、Usha Singh、Mohindra S. Chadha、Vasant R. Mamdapur

  DOI：10.1246/bcsj.66.1566

  日期：1993.5

  A one pot synthesis of peptides with free C-terminal residues has been accomplished via the active Se-phenyl carboselenoate using diphenyl diselenide, tributylphosphine, and N-methylmorpholine N-oxide in an acetonitrile– water mixed solvent system. Free amino acids and peptides have been used as the amine component without pH adjustment.

  通过活性硒代苯基羧硒酸酯，利用二苯基二硒化物、三丁基膦和N-甲基吗啉N-氧化物在丙酮腈-水混合溶剂体系中，实现了具有自由C端残基的多肽的一锅法合成。无需pH调节，自由氨基酸和多肽被用作氨基组分。
• Synthesis and Anti-Helicobacter pylori Activity of Pyloricidin Derivatives. I. Structure-activity Relationships on the Terminal Peptidic Moiety.
  作者：ATSUSHI HASUOKA、YUJI NISHIKIMI、YUTAKA NAKAYAMA、KEIJI KAMIYAMA、MASAFUMI NAKAO、KEN-ICHIRO MIYAGAWA、OSAMU NISHIMURA、MASAHIKO FUJINO

  DOI：10.7164/antibiotics.55.322

  日期：——

  The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing α-D-, β- and γ-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with α-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allylglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006μg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.

  新型天然抗生素喷菌素A、B和C对幽门螺杆菌具有强效且高度选择性的抗菌活性。为了研究末端肽部分的结构-活性关系，制备了一系列含不同氨基酸的喷菌素B和喷菌素C衍生物，并评估了它们的抗幽门螺杆菌活性。含有α-D-、β-和γ-氨基酸或肽模拟物的衍生物显示出显著降低的活性。另一方面，含有α-L-氨基酸的衍生物被发现能保持活性。在本工作中制备的衍生物中，烯丙基甘氨酸衍生物2s表现出最强的抗幽门螺杆菌活性，对幽门螺杆菌NCTC11637的最低抑制浓度（MIC）值小于0.006μg/ml，比原始化合物喷菌素C的活性高出60倍。
• [EN] INDOLE DERIVATIVES AS EFFLUX PUMP INHIBITORS<br/>[FR] DÉRIVÉS D'INDOLE UTILISÉS EN TANT QU'INHIBITEURS DE POMPE D'EFFLUX
  申请人：LAVOIE EDMOND J

  公开号：WO2018165611A1

  公开（公告）日：2018-09-13

  Disclosed herein are compounds of formula (I): and salts thereof. Also disclosed are compositions comprising compounds of formula I and compounds of formula I for use in treating or preventing bacterial infections.

  本文披露了以下式(I)的化合物及其盐。还披露了包含式I化合物的组合物和用于治疗或预防细菌感染的式I化合物。