Nα-CBZ-Nω-硝基-L-精氨酸 | 2304-98-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 精氨酸类衍生物
• 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: Nα-CBZ-Nω-硝基-L-精氨酸
• 中文别名: 苄氧羰基-N'-硝基-L-精氨酸；NAlpha-CBZ-Nω-硝基-L-精氨酸；N-CBZ-硝基-精氨酸；CBZ-N'-硝基-L-精氨酸；Cbz-N"-硝基-L-精氨酸； 苄氧羰基-N"-硝基-L-精氨酸；苄氧羰基-硝基-L-精氨酸
• 英文名称: N5-[imino(nitroamino)methyl]-N2-[(phenylmethoxy)carbonyl]-L-ornithine
• 英文别名: N-(benzyloxycarbonyl)-N^ω-nitro-L-arginine；N^α-benzyloxycarbonyl-N^ω-nitroarginine；N^α-Cbz-L-Arg^NO2；N_α-(carbonyloxybenzyl)-N_ω-nitro-L-arginine；N^α-(Z)-N^ω-nitro-L-arginine；N^α-benzyloxycarbonyl-N^ω-nitro-L-arginine；N^α-Benzyloxycarbonyl-N^ω-nitro-L-arginin；N^ω-Nitro-N^α-benzyloxycarbonyl-L-arginin；N(α)-Z-N(ο)-nitro-L-arginine；Cbz-Arg(NO₂)-OH；L-Nα-carbobenzoxy,Nω-nitroarginine；(2S)-5-[amino(nitramido)methylidene]azaniumyl-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 2304-98-5
• 化学式: C₁₄H₁₉N₅O₆
• mdl: MFCD00038092
• 分子量: 353.335
• InChiKey: BZPCSFNCKORLQG-NSHDSACASA-N

物化性质

• 熔点：
  130-132 °C (dec.)
• 密度：
  1.44±0.1 g/cm3(Predicted)
• 溶解度：
  少量溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2925290090
• 包装等级：
  III
• 危险类别：
  4.1
• 危险性防范说明：
  P261,P210,P264,P280,P370+P378,P302+P352+P312
• 危险品运输编号：
  1325
• 危险性描述：
  H302+H312+H332,H315,H319,H228
• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  Nα-CBZ-Nω-硝基-L-精氨酸 在 copper acetylacetonate 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 N-苄氧羰基-L-精氨酸
  参考文献：
  名称：

  NaBH4 – a novel method for the deprotection of Nω-nitro-arginine

  摘要：

  The selective deprotection of N-omega-nitro-arginine derivatives represents a major preparative challenge. This problem can be circumvented by the use of catalytic hydrogenation, but often high pressure, elevated temperature, and/or long reaction times are needed. In certain cases hydrogenation is not suitable, for example, small-scale reactions, parallel synthesis, or due to selectivity issues. Herein, we demonstrate for the first time, the use of NaBH4 in the presence of a metal ion catalyst for the removal of the N-omega-nitro moiety under simple, 'open-vessel' conditions. This process using NaBH4 does not remove the benzyloxycarbonyl-protecting group; thus the method is orthogonal for this protecting scheme. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.12.081
• 作为产物：
  描述：

  L-精氨酸盐酸盐 在 sodium hydroxide 、 硫酸 、 三氧化硫 、 硝酸 、 二氧化氮 作用下， 生成 Nα-CBZ-Nω-硝基-L-精氨酸
  参考文献：
  名称：

  Gibian,H.; Schroeder,E., Justus Liebigs Annalen der Chemie, 1961, vol. 642, p. 145 - 162

  摘要：

  DOI：

文献信息

• Synthesis of the octadecapeptide corresponding to positions 32 to 49 of the revised amino acid sequence of thymopoietin II and its effect on low E-rosette forming cells of an aged patient with chronic renal failure.
  作者：TAKASHI ABIKO、HIROSHI SEKINO

  DOI：10.1248/cpb.30.3271

  日期：——

  The octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH, corresponding to positions 32 to 49 of the revised amino acid sequence of bovine thymopoietin II was synthesized by the azide condensation of three fragments, (32-36), (37-41) and (42-49), followed by deprotection with hydrogen fluoride in the presence of anisole-thioanisole-o-cresol. The in vitro addition of the synthetic thymopoietin II (32-49) significantly restored the low E-rosette forming capacity of cells from an aged patient with chronic renal failure to normal levels. The in vitro effect of [Gln38, Thr43, Val47]-thymopoietin II (32-49) on the low E-rosette forming capacity of cells from the aged patient with chronic renal failure was also compared with that of the synthetic thymopoietin II (32-49). The [Gln38, Thr43, Val47]-thymopoietin II (32-49) was approximately equipotent with the synthetic thymopoietin II (32-49) at a concentration of 100 μg/ml.

  十八肽H-Arg-Lys-Asp-Val-Tyr-Val-Glu-Leu-Tyr-Leu-Gln-Ser-Leu-Thr-Ala-Leu-Lys-Arg-OH，对应于牛胸腺生成素II修订后的氨基酸序列的第32至49位，通过三个片段(32-36)、(37-41)和(42-49)的叠氮化物缩合合成，随后在茴香硫醚-邻甲酚存在下用氢氟酸脱保护。体外添加合成的胸腺生成素II(32-49)显著恢复了来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力至正常水平。[Gln38, Thr43, Val47]胸腺生成素II(32-49)对来自慢性肾衰竭老年患者的细胞的低E玫瑰花形成能力的影响也与合成的胸腺生成素II(32-49)进行了比较。在100 μg/ml的浓度下，[Gln38, Thr43, Val47]胸腺生成素II(32-49)与合成的胸腺生成素II(32-49)大致等效。
• Lipophilic and hydrophilic esters of 4-acetyl-2-(2-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one as antihypertensive agents
  作者：S. W. Fogt、J. A. Scozzie、R. D. Heilman、L. J. Powers

  DOI：10.1021/jm00186a030

  日期：1980.12

  In an attempt to enhance the antihypertensive activity of 4-acetyl-2-(2-hydroxyethyl)-5,6-bis(4-chlorophenyl)-2H-pyridazin-3-one, 1, a series of lipophilic and hydrophilic esters was synthesized. These derivatives possessed increased lipid and aqueous solubility, respectively. The esters, in general, cause a larger blood-pressure drop than 1 when tested at high doses in the spontaneously hypertensive

  为了增强4-乙酰基-2-（2-羟乙基）-5,6-双（4-氯苯基）-2H-哒嗪-3-one，1的抗高血压活性，制备了一系列亲脂性和亲水性酯合成的。这些衍生物分别具有增加的脂质和水溶性。通常，当在自发性高血压大鼠（SHR）模型中以高剂量进行测试时，这些酯类引起的血压下降大于1。在较低剂量下，抗高血压活性与1相同。
• Synthesis of Mesoionic Triazolopyridine. III. Applications of<i>N</i>-Acyl Mesoionic Triazolopyridines as Acylating Reagents
  作者：Akio Saito、Bunji Shimizu

  DOI：10.1246/bcsj.56.2974

  日期：1983.10

  Utility of N-acyl mesoionic triazolopyridines as acylating reagents was investigated concerning with peptide synthesis. Several dipeptides and N-alkoxycarbonyl amino acids were prepared by use of these reagents.

  研究了N-酰基中井杂环三唑吡啶作为酰化试剂在肽合成中的应用。利用这些试剂制备了几种二肽和N-烷氧羰基氨基酸。
• Peptide Synthesis in Aqueous Solution. IV. Preparation and Properties of [<i>p</i>-(Benzyloxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Z-ODSP), [<i>p</i>-(<i>t</i>-Butoxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Boc-ODSP) and [<i>p</i>-(9-Fluorenylmethyloxycarbonyloxy)phenyl]dimethylsulfonium Methyl Sulfate (Fmoc-ODSP) as Water-Soluble<i>N</i>-Acylating Reagents
  作者：Ikunori Azuse、Masahiro Tamura、Keisuke Kinomura、Hideo Okai、Katsushige Kouge、Fumio Hamatsu、Tatsuya Koizumi

  DOI：10.1246/bcsj.62.3103

  日期：1989.10

  order to increase the applications of the water-soluble active ester method, water-soluble acylating reagents, [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate and [p-(9-fluorenylmethyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, were synthesized from of p-hydroxyphenyldimethylsulfonium methyl sulfate. These

  为了增加水溶性活性酯法的应用，水溶性酰化试剂[对(苄氧基羰基氧基)苯基]二甲基硫酸锍、[对(叔丁氧基羰氧基)苯基]二甲基硫酸锍和[对- (9-芴基甲氧基羰基氧基)苯基]二甲基锍甲基硫酸盐由对羟基苯基二甲基锍甲基硫酸盐合成。这些化合物在水中具有高溶解度（超过 30%），并且被发现可作为优异的水溶性酰化试剂，用于在水溶液中合成 N-苄氧羰基、N-叔丁氧羰基、N-9-芴基甲氧羰基氨基酸衍生物。他们在水性介质和氨基酸中将二肽转化为 N-酰基二肽。此外，还发现它们是保护赖氨酸、鸟氨酸、
• Low molecular weight, non-peptide fibrinogen receptor antagonists
  作者：Leo Alig、Albrecht Edenhofer、Paul Hadvary、Marianne Huerzeler、Dietmar Knopp、Marcel Mueller、Beat Steiner、Arnold Trzeciak、Thomas Weller

  DOI：10.1021/jm00101a017

  日期：1992.11

  selectivity for GP IIb-IIIa vs the closely related vitronectin receptor alpha v beta 3. By random screening [(p-amidinobenzenesulfonamido)ethyl]-p-phenoxyacetic acid derivatives have been identified as fibrinogen receptor antagonists. Further structure-activity relationship studies culminated in the preparation of N-[N-[N-(p-amidinobenzoyl)-beta-alanyl]-L-alpha-aspartyl]-3-phenyl-L- alanine (29h, Ro 43-5054)

  四肽H-Arg-Gly-Asp-Ser-OH（1）（RGDS）代表血纤维蛋白原对其血小板受体GP IIb-IIIa（整联蛋白alpha IIb beta 3）的识别序列，是开发GSH的主要化合物。高效和选择性的纤维蛋白原受体拮抗剂。用对-d基苯丙氨酸替换N-末端精氨酸或用间氨基苯甲酸替换Gly部分，使得化合物在GP IIb-IIIa的活性和选择性方面优于紧密连接的玻连蛋白受体αv beta 3.通过随机筛选[（对-氨基苯磺酰胺基）乙基]-对-苯氧基乙酸衍生物已鉴定为纤维蛋白原受体拮抗剂。