L-(+)-citrulline ethyl ester | 80822-58-8

• 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: L-(+)-citrulline ethyl ester
• 英文别名: L-citrulline ethyl ester；L-citrulline ethylester；ethyl (2S)-2-amino-5-(carbamoylamino)pentanoate
• CAS: 80822-58-8
• 化学式: C₈H₁₇N₃O₃
• 分子量: 203.241
• InChiKey: QONFNFTXYLVVLM-LURJTMIESA-N

物化性质

• 沸点：
  324.1±42.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氰胺 、 L-(+)-citrulline ethyl ester 在 盐酸 、 sodium amalgam 作用下， 生成 2-amino-4(5)-(3-ureidopropyl)imidazole
  参考文献：
  名称：

  Biomimetic synthesis of dibromophakellin

  摘要：

  DOI：

  10.1021/ja00370a072
• 作为产物：
  描述：

  乙基N5-(二氨基亚甲基)-L-鸟氨酰i噻吩基n酸酯 在 alpha-酮戊二酸 、 bovine liver glutamate dehydrogenase type II 、 recombinant Giardia lamblia arginine deiminase 、 水 作用下， 生成 L-(+)-citrulline ethyl ester
  参考文献：
  名称：

  Mechanisms of catalysis and inhibition operative in the arginine deiminase from the human pathogen Giardia lamblia

  摘要：

  Giardia lamblia arginine deiminase (GlAD), the topic of this paper, belongs to the hydrolase branch of the guanidine-modifying enzyme superfamily, whose members employ Cys-mediated nucleophilic catalysis to promote deimination of L-arginine and its naturally occurring derivatives. G. lamblia is the causative agent in the human disease giardiasis. The results of RNAi/antisense RNA gene-silencing studies reported herein indicate that GlAD is essential for G. lamblia trophozoite survival and thus, a potential target for the development of therapeutic agents for the treatment of giardiasis. The homodimeric recombinant protein was prepared in Escherichia coli for in-depth biochemical characterization. The 2-domain GlAD monomer consists of a N-terminal domain that shares an active site structure (depicted by an in silico model) and kinetic properties (determined by steady-state and transient state kinetic analysis) with its bacterial AD counterparts, and a C-terminal domain of unknown fold and function. GlAD was found to be active over a wide pH range and to accept L-arginine, L-arginine ethyl ester, N-alpha-benzoyl-L-arginine, and N-omega-amino-L-arginine as substrates but not agmatine, L-homoarginine, N-alpha-benzoyl- L-arginine ethyl ester or a variety of arginine-containing peptides. The intermediacy of a Cys424-alkylthiouronium ion covalent enzyme adduct was demonstrated and the rate constants for formation (k(1) = 80 s(-1)) and hydrolysis (k(2) = 35 s(-1)) of the intermediate were determined. The comparatively lower value of the steady-state rate constant (k(cat) = 2.6 s(-1)), suggests that a step following citrulline formation is rate-limiting. Inhibition of GlAD using Cys directed agents was briefly explored. S-Nitroso-L-homocysteine was shown to be an active site directed, irreversible inhibitor whereas N omega-cyano-L-arginine did not inhibit GlAD but instead proved to be an active site directed, irreversible inhibitor of the Bacillus cereus AD. (C) 2009 Published by Elsevier Inc.

  DOI：

  10.1016/j.bioorg.2009.06.001

文献信息

• METHOD OF TREATMENT AND PREVENTION OF NITRIC OXIDE DEFICIENCY-RELATED DISORDERS WITH CITRULLINE AND CITRULLINE DERIVATIVES
  申请人：——

  公开号：US20010056068A1

  公开（公告）日：2001-12-27

  The invention provides methods for control, management, treatment and prevention of conditions related to nitric oxide deficiency such as hypertension, cardiovascular disease, osteoporosis, diabetes mellitus, preeclampsia HELLP, syndrome and fetal growth retardation; uterine contractility disorders such as preterm labor and dysmenorrhea, cervical dystocia, infertility and early pregnancy loss; male impotence; urinary incontinence; intestinal tract disorders (e.g. altered motility and pyloric stenosis), respiratory system diseases (e.g. asthma, neonatal respiratory distress syndrome, pulmonary hypertension, and adult respiratory distress syndrome); inflammatory diseases (e.g. acute inflammation, resistance to infection, SLE-lupus, anaphylactic reaction, allograft rejection); Alzheimer's disease, stroke, growth hormone disorders, and behavior changes; dermatological conditions such as atopic eczema, topical hair loss, and burn injury; by administering citrulline or a citrulline analogue, optionally in combination with other enhancing or modulating agents, e.g., an estrogenic, partial estrogenic, progestagenic, or androgenic agent, and pharmaceutical preparations for such uses.

  本发明提供了控制、管理、治疗和预防与一氧化氮缺乏相关的疾病的方法，例如高血压、心血管疾病、骨质疏松症、糖尿病、先兆子痫HELLP综合症和胎儿生长迟缓；子宫收缩障碍，如早产和痛经、宫颈难产、不孕症和早期妊娠流产；男性阳痿；尿失禁；肠道疾病（例如肠动力障碍和幽门狭窄）、呼吸系统疾病（例如哮喘、新生儿呼吸窘迫综合症、肺动脉高压和成人呼吸窘迫综合症）；炎症性疾病（例如急性炎症、对感染的抵抗力、SLE-狼疮、过敏反应、移植排斥）；阿尔茨海默病、中风、生长激素障碍和行为改变；皮肤病，如特应性湿疹、局部脱发和烧伤；通过给予瓜氨酸或瓜氨酸类似物，可选择与其他增强或调节剂（例如雌激素、部分雌激素、孕激素或雄激素）以及用于此类用途的制药制剂联合使用。
• PRODUIT DE COMBINAISON POUR LE TRAITEMENT DU SURPOIDS ET/OU L'AMÉLIORATION DE LA SILHOUETTE
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：EP2819635A1

  公开（公告）日：2015-01-07
• COMBINATION THERAPY TO INCREASE ENDOGENOUS NITRIC OXIDE (NO) SYNTHESIS
  申请人：Yeda Research and Development Co., Ltd.

  公开号：EP3481386A1

  公开（公告）日：2019-05-15
• US5304470A
  申请人：——

  公开号：US5304470A

  公开（公告）日：1994-04-19
• [EN] COMBINATION PRODUCT FOR TREATING EXCESS WEIGHT AND/OR FOR IMPROVING THE FIGURE<br/>[FR] PRODUIT DE COMBINAISON POUR LE TRAITEMENT DU SURPOIDS ET/OU L'AMÉLIORATION DE LA SILHOUETTE
  申请人：AGRONOMIQUE INST NAT RECH

  公开号：WO2013128137A1

  公开（公告）日：2013-09-06

  L'invention concerne un produit de combinaison comprenant à titre de substances actives, au moins un inhibiteur de l'enzyme HMG-CoA-réductase et la citrulline ou un composé bioéquivalent de celle-ci pour le traitement du surpoids ou de l'obésité et/ou de l'accumulation de masse grasse. L'invention concerne également un procédé de traitement cosmétique pour améliorer ou affiner la silhouette et/ou stimuler la perte de poids superflu et/ou de cellulite et/ou limiter son accumulation, comprenant l'administration d'un produit de combinaison comprenant à titre de substances actives, au moins un inhibiteur de l'enzyme HMG-CoA-réductase ou un sel physiologiquement acceptable de celle-ci, et la citrulline ou un composé bioéquivalent de celle- ci, ou l'un de leurs analogues et le renouvellement de ladite administration jusqu'à obtention de l'effet cosmétique désiré. L'invention concerne enfin l'utilisation d'un produit de combinaison tel que précédemment défini pour améliorer ou affiner la silhouette et/ou stimuler la perte de poids superflu et/ou de cellulite et/ou limiter son accumulation.