L(+)-n-cbz-鸟氨酸盐酸盐 | 92455-59-9

• 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: L(+)-n-cbz-鸟氨酸盐酸盐
• 英文名称: N^α-benzyloxycarbonyl-L-ornithine hydrochloride
• 英文别名: N-Z-Orn(^δN*HCl)；Nα-Z-L-Orn*HCl；Z-Orn-OH HCl；N²-benzyloxycarbonyl-L-ornithine ; hydrochloride；N²-Benzyloxycarbonyl-L-ornithin; Hydrochlorid；(S)-5-Amino-2-(((benzyloxy)carbonyl)amino)pentanoic acid hydrochloride；(2S)-5-amino-2-(phenylmethoxycarbonylamino)pentanoic acid;hydrochloride
• CAS: 92455-59-9
• 化学式: C₁₃H₁₈N₂O₄*ClH
• 分子量: 302.758
• InChiKey: ULELFCUZAINLJV-MERQFXBCSA-N

物化性质

• 熔点：
  187-189 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  L(+)-n-cbz-鸟氨酸盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  从氨基酸实际合成游离和受保护的胍基酸

  摘要：

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。

  DOI：

  10.1016/0040-4039(96)00299-7
• 作为产物：
  描述：

  N-苄氧羰基-N’-叔丁氧羰基-L-鸟氨酸 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以22.76 g的产率得到L(+)-n-cbz-鸟氨酸盐酸盐
  参考文献：
  名称：

  Masiukiewicz, Elzbieta; Wiejak, Stanislaw; Rzeszotarska, Barbara, Organic Preparations and Procedures International, 2002, vol. 34, # 5, p. 531 - 537

  摘要：

  DOI：

文献信息

• ORNITHINE DERIVATIVE
  申请人：Astellas Pharma Inc.

  公开号：EP2141147A1

  公开（公告）日：2010-01-06

  Provided is a compound which is useful as a therapeutic agent for chronic renal insufficiency and a therapeutic agent for diabetic nephropathy. The present inventors have made extensive studies on an ornithine derivative having an antagonistic action against an EP4 receptor, and as a result, they have found that by introducing cycloalkanediyl at a C terminal of the ornithine part of the compound of the present invention, the physicochemical properties such as solubility, and the like can be improved, thereby giving further preferred properties as a pharmaceutical. Therefore, they have completed the present invention. The compound of the present invention exhibits a good antagonistic action against an EP4 receptor, and thus, it is useful as a therapeutic agent for chronic renal insufficiency and diabetic nephropathy.

  提供了一种化合物，可用作慢性肾功能不全的治疗剂和糖尿病肾病的治疗剂。目前的发明人对具有对EP4受体拮抗作用的鸟氨酸衍生物进行了广泛研究，结果发现通过在目前发明的化合物的鸟氨酸部分的C末端引入环烷基，可以改善物理化学性质，如溶解性等，从而赋予其作为药物的更优越性质。因此，他们完成了这项发明。目前发明的化合物对EP4受体表现出良好的拮抗作用，因此，它可用作慢性肾功能不全和糖尿病肾病的治疗剂。
• [EN] THE TOTAL SYNTHESIS OF GLUCOSEPANE AND COMPOUNDS OBTAINED THEREFROM<br/>[FR] SYNTHÈSE TOTALE DE GLUCOSÉPANE ET COMPOSÉS OBTENUS À PARTIR DE CELLE-CI
  申请人：UNIV YALE

  公开号：WO2017053776A1

  公开（公告）日：2017-03-30

  Glucosepane is a structurally complex protein post-translational modification (PTM) believed to exist in all living organisms. Research in humans suggests that glucosepane plays a critical role in the pathophysiology of both diabetes and human aging; yet comprehensive biological investigations of this 'metabolite have been 'greatly hindered by a scarcity of chemically homogeneous material available for study. Glucosepane possesses a unique chemical structure that incorporates a surprising, never-before-prepared non-aromatic tautomer of imidazole (hereafter termed an "iso-imidazole"), rendering it a challenging target for chemical synthesis. In this application, the inventors report the first total synthesis of glucosepane, enabled by the development of a novel one-pot method for preparation of the iso-imidazole core. The synthesis of the present invention is concise (8-steps starting from commercial materials), convergent, high-yielding (12% overall), and enantioselective. These results should prove useful to the art and practice of heterocyclic chemistry, and critical for the study of glucosepane and its role in human health and disease, especially the treatment of diabetic disorders or its impact on aging processes. Methods of synthesis, compounds obtained therefrom, pharmaceutical compositions and methods of treatment provide embodiments of the present invention.

  葡萄糖胺是一种结构复杂的蛋白后翻译修饰（PTM），被认为存在于所有生物体中。人类的研究表明，葡萄糖胺在糖尿病和人类衰老的病理生理学中起着关键作用；然而，对这种“代谢产物”的全面生物学研究受到可供研究的化学均一材料的稀缺性的极大阻碍。葡萄糖胺具有独特的化学结构，其中包含一个令人惊讶的、从未制备过的非芳香咪唑互变异构体（以下简称“异咪唑”），使其成为化学合成的一个具有挑战性的目标。在本申请中，发明人报告了葡萄糖胺的首次全合成，该合成是通过开发一种新型一锅法制备异咪唑核心而实现的。本发明的合成方法简明（从商业材料开始的8步），收率高（总体为12%），对映选择性高。这些结果应该对杂环化学的艺术和实践有用，并且对研究葡萄糖胺及其在人类健康和疾病中的作用、特别是治疗糖尿病或其对衰老过程的影响至关重要。本发明提供了合成方法、从中获得的化合物、制药组合物和治疗方法的实施例。
• 15N NMR spectroscopy. 30—structure/shift relationships of oligopeptides and copolypeptides, including gramicidin S
  作者：Hans R. Kricheldorf

  DOI：10.1002/mrc.1270150211

  日期：1981.2

  AbstractThe 15N NMR spectra of various oligopeptide derivatives of the ZXYYOMe structure, where X and Y are variable amino acids and Z is the benzyloxycarbonyl group, were measured in several protic and aprotic solvents. The shift difference of the 15N of the YY and XY bond (neighbouring residue effect) is discussed with respect to the nature of X and Y with respect to the solvent. Oligopeptides of the ZXYYOH and n̊H3XYYOMe structures were compared with the Z‐pëptide esters to investigate the spectroscopic influence of the protecting groups. The methyl ester hydrochlorides of the 25 most common amino acids were measured in water and DMSO to elucidate the solvent dependence of the substituent effects. Moreover, the methyl ester hydrochlorides were compared with Z‐amino acids and N‐acetyl‐amino acid methyl esters in DMSO to establish whether the substituent effects depend on the nature of the amino acid derivatives. In this connection the assignments of the serine, threonine and glycine signals are discussed with respect to silk proteins. Furthermore, the assignments of the signals of copolypeptides by comparison with oligo‐ and homo‐polypeptides are discussed. Finally, it was demonstrated that intramolecular H bonds cause downfied shifts of 7–10 ppm of the acceptor amide groups.
• US8030489B2
  申请人：——

  公开号：US8030489B2

  公开（公告）日：2011-10-04
• A practical synthesis of free and protected guanidino acids from amino acids
  作者：Bansi Lal、A.K. Gangopadhyay

  DOI：10.1016/0040-4039(96)00299-7

  日期：1996.4

  Synthesis of protected guanidino acids in one pot reaction is achieved. Amino acids are treated with trimethylsilyl chloride, triethylamine, dicarbobenzoxy-S-methyl isothiourea in dichloromethane followed by removal of silyl group by treatment with methanol to give the corresponding carbobenzoxy guanidino acids.

  在一锅反应中合成了受保护的胍基酸。用二氯甲烷中的三甲基甲硅烷基氯，三乙胺，二碳苯甲氧基-S-甲基异硫脲处理氨基酸，然后通过用甲醇处理除去甲硅烷基，得到相应的碳苯甲酰胍基酸。