N^α-(tert-butyloxycarbonyl)-D-norvaline tert-butyl ester | 149970-79-6

• 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: N^α-(tert-butyloxycarbonyl)-D-norvaline tert-butyl ester
• 英文别名: N2-Boc-D-ornithine tert-butyl ester；tert-butyl (2R)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoate
• CAS: 149970-79-6
• 化学式: C₁₄H₂₈N₂O₄
• 分子量: 288.387
• InChiKey: XXIQPSQYSBWVII-SNVBAGLBSA-N

物化性质

• 沸点：
  392.6±37.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  N^α-(tert-butyloxycarbonyl)-D-norvaline tert-butyl ester 在 盐酸 、 一水合肼 作用下， 以 1,4-二氧六环 、 乙醇 、 异丙醇 为溶剂， 反应 29.0h， 生成 N^δ-(5-amino-2H-1,2,4-triazol-3-yl)-D-ornithine
  参考文献：
  名称：

  Methodology for the preparation of N-guanidino-modified arginines and related derivatives

  摘要：

  Methods for the preparation of N(G)-modified arginines and N(delta)-heterocyclic ornithines are described. The reactive cyanamide intermediate tert-butyl N(alpha)-Boc-N(delta)-cyano-L-ornithinate (2). prepared either by treatment of tert-butyl N(alpha)-BOC-L-ornithinate (5) with cyanogen bromide or by dehydration of tert-butyl N(alpha)-Boc-L-citrullinate (6), was utilized to prepare N(G)-hydroxy-L-arginine, N(G)-amino-L-arginine, and N(G)-methoxy-L-arginine. Intermediates 3a and 3b, derived from treatment of 5 with diphenyl cyanocarbonimidate (19), reacted with nitrogen nucleophiles to produce novel N(G)-cyano-L-arginine and N(delta)-heterocyclic L-ornithine analogs.

  DOI：

  10.1021/jo00068a031
• 作为产物：
  描述：

  (R)-2-tert-Butoxycarbonylamino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoic acid tert-butyl ester 在 哌啶 作用下， 以 氯仿 为溶剂， 生成 N^α-(tert-butyloxycarbonyl)-D-norvaline tert-butyl ester
  参考文献：
  名称：

  Selective Substrate-Based Inhibitors of Mammalian Dimethylarginine Dimethylaminohydrolase

  摘要：

  The enzyme DDAH metabolizes methylarginines that are inhibitors of nitric oxide synthase (NOS). Substrate-based inhibitors of mammalian DDAH have been synthesized, with optimization to give selective inhibition of DDAH with no significant direct effect on NOSs. These are the first examples of reversible DDAH inhibitors with significant activity and selectivity. In vivo administration increases plasma ADMA levels, giving proof of concept that these inhibitors can be used to probe the physiological effects of DDAH inhibition, with potential for pharmaceutical use of DDAH inhibitors in diseases where excess NO production is implicated.

  DOI：

  10.1021/jm050187a

文献信息

• Synthesis and Precursor-Directed Biosynthesis of New Hormaomycin Analogues
  作者：Boris D. Zlatopolskiy、Markus Radzom、Axel Zeeck、Armin de Meijere

  DOI：10.1002/ejoc.200500856

  日期：2006.3

  Several new analogues of hormaomycin (1), a peptide lactone with interesting biological activities, were prepared by total synthesis or by precursor-directed biosynthesis. The new analogues 2a–c, 3a–c, O-MOM-1 and epi-O-MOM-1 as well as the model acyl tripeptides 20a–c and 21a–e were tested for their antibiotic activities to give new insights into structure–activity relationships of this class of compounds

  激素 (1) 的几种新类似物（一种具有有趣生物活性的肽内酯）是通过全合成或前体定向生物合成制备的。测试了新的类似物 2a-c、3a-c、O-MOM-1 和 epi-O-MOM-1 以及模型酰基三肽 20a-c 和 21a-e 的抗生素活性，以提供对结构的新见解——这类化合物的活性关系。在这种情况下，发现了 2c 对白色念珠菌的意外活性。进料实验所需的前体氨基酸 14a、14b 和 17 分别通过 4 和 3 个步骤以 31、48 和 55% 的产率制备。此外，这些研究提供了一些关于提供化合物 1 的生物合成途径的新信息。他们还支持这样一种观点，即化学和生物方法的结合可以提供一种有趣的具有生物活性的天然产物的广泛类似物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Enzymatic Tailoring of Ornithine in the Biosynthesis of the <i>Rhizobium</i> Cyclic Trihydroxamate Siderophore Vicibactin
  作者：John R. Heemstra、Christopher T. Walsh、Elizabeth S. Sattely

  DOI：10.1021/ja9056008

  日期：2009.10.28

  To acquire iron, the N-2-fixing, symbiotic bacterium Rhizobium sp. produce the cyclic trihydroxamate siderophore vicibactin, containing a 30-membered trilactone scaffold. Herein we report the overproduction and purification of the six proteins VbsACGOLS in the bacterial host Escherichia coli and the reconstitution of the biosynthesis of vicibactin from primary metabolites. The flavoprotein VbsO acts as a pathway-initiating L-ornithine M-hydroxylase, followed by VbsA, which transfers (R)-3-hydroxybutyryl- from the CoA thioester to N-6-hydroxyornithine to yield N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-L-orinithine. VbsL is a PLP-dependent epimerase acting at C-2 of the 10 atom monomer unit. VbsS, a nonribosomal peptide synthetase freestanding module, then activates N-6-((R)-3-hydroxybutyryl)-N-6-hydroxy-D-ornithine as the AMP anhydride on the way to cyclotrimerization to the vicibactin scaffold. The last step, tris-acetylation of the C-2 amino group of desacetyl-D-vicibactin to the mature siderophore vicibactin, is catalyzed distributively by VbsC, using three molecules of acetyl-CoA.
• Synthesis of the trans-fusarinine scaffold
  作者：Samuel Bertrand、Olivier Duval、Jean-Jacques Hélesbeux、Gérald Larcher、Pascal Richomme

  DOI：10.1016/j.tetlet.2010.02.058

  日期：2010.4

  The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of N-alpha-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from L-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone. (c) 2010 Elsevier Ltd. All rights reserved.
• Narayanan; Griffith, Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 885 - 887
  作者：Narayanan、Griffith

  DOI：——

  日期：——
• Methodology for the preparation of N-guanidino-modified arginines and related derivatives
  作者：Frank L. Wagenaar、James F. Kerwin

  DOI：10.1021/jo00068a031

  日期：1993.7

  Methods for the preparation of N(G)-modified arginines and N(delta)-heterocyclic ornithines are described. The reactive cyanamide intermediate tert-butyl N(alpha)-Boc-N(delta)-cyano-L-ornithinate (2). prepared either by treatment of tert-butyl N(alpha)-BOC-L-ornithinate (5) with cyanogen bromide or by dehydration of tert-butyl N(alpha)-Boc-L-citrullinate (6), was utilized to prepare N(G)-hydroxy-L-arginine, N(G)-amino-L-arginine, and N(G)-methoxy-L-arginine. Intermediates 3a and 3b, derived from treatment of 5 with diphenyl cyanocarbonimidate (19), reacted with nitrogen nucleophiles to produce novel N(G)-cyano-L-arginine and N(delta)-heterocyclic L-ornithine analogs.