tert-butyl (S)-5-amino-2-(benzyloxycarbonylamino)pentanoate | 26302-90-9

• 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: tert-butyl (S)-5-amino-2-(benzyloxycarbonylamino)pentanoate
• 英文别名: Benzyloxycarbonyl-L-ornithine tert-butyl ester；tert-butyl (2S)-5-amino-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 26302-90-9
• 化学式: C₁₇H₂₆N₂O₄
• 分子量: 322.404
• InChiKey: GKULKEDYZKGYOH-AWEZNQCLSA-N

物化性质

• 沸点：
  467.2±45.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  tert-butyl (S)-5-amino-2-(benzyloxycarbonylamino)pentanoate 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 sodium carbonate 、 三氟乙酸 作用下， 反应 0.67h， 生成 delta-N-乙酰基-delta-N-羟基-L-鸟氨酸
  参考文献：
  名称：

  氨基酸氧化。第五部分：由赖氨酸合成N 6-乙酰-N 6-羟基赖氨酸的新方法

  摘要：

  通过用过氧化苯甲酰氧化N 2-苄氧基羰基-L-赖氨酸叔丁酯中的氨基，并随后乙酰化，由L-赖氨酸合成N 6-乙酰基-N 6 -L-羟基赖氨酸。

  DOI：

  10.1016/s0040-4039(00)95430-3
• 作为产物：
  描述：

  tert-butyl (S)-5-azido-2-(benzyloxycarbonylamino)pentanoate 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以73%的产率得到tert-butyl (S)-5-amino-2-(benzyloxycarbonylamino)pentanoate
  参考文献：
  名称：

  Synthesis of unnatural homologues of deoxypyridinoline as possible internal standards in analytical detection of pyridinolinic cross-links of collagen

  摘要：

  Three homologues of the collagen cross-links deoxypyridinoline, differing in the length of the side chain at the aromatic nitrogen, have been efficiently synthesized as possible internal standards in the quantitative analyses of pyridinolines. The first has a one-carbon shorter N-chain, while other two have a one-carbon and a two-carbon longer N-chain. The stereogenic centers are introduced stereoselectively using Williams' glycine template methodology and oxazinones to generate chirality and to suitably protect the amino acid functionality during assembly of the pyridinoline nucleus. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.001

文献信息

• Method for the treatment of hypotension induced by a cytokine or
  申请人：The Medical College of Wisconsin Research Foundation, Inc.

  公开号：US05476871A1

  公开（公告）日：1995-12-19

  Inhibitors of nitric oxide formation from arginine useful for treating hypotension, inflammation, stroke and to restore vascular contractile sensitivity to the effects of .alpha..sub.1 -adrenergic agonists are physiologically active compounds including N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties or monoalkyl carbon-substituted N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties, having the formula ##STR1## wherein R is (CH.sub.2).sub.y CH.sub.3 or H, R' is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, and R" is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, with y ranging from 0 to 5, and x is 0 or 1 and wherein none or only one of R, R' and R" provides an alkyl substituent on ornithine or lysine moiety, and wherein Q is alkyl having 1 to 5 carbon atoms, and physiologically acceptable acid addition salts thereof.

  阻止精氨酸生成一氧化氮的抑制剂，可用于治疗低血压、炎症、中风，并恢复血管对α1-肾上腺素能受体激动剂的收缩敏感性，这些生理活性化合物包括Nδ-取代鸟氨酸或Nε-取代赖氨酸基团或单烷基碳取代Nδ-取代鸟氨酸或Nε-取代赖氨酸基团，其化学式为##STR1## 其中R为（CH2）yCH3或H，R'为CH2或C（H）（CH2）yCH3，R"为CH2或C（H）（CH2）yCH3，y在0到5之间，x为0或1，其中R、R'和R"中的任何一个或仅一个在鸟氨酸或赖氨酸基团上提供烷基取代基，Q为具有1至5个碳原子的烷基，以及其生理上可接受的酸盐。
• Heme binding compounds and use thereof
  申请人：The Medical College of Wisconsin Research Foundation, Inc.

  公开号：US05663364A1

  公开（公告）日：1997-09-02

  Inhibitors of nitric oxide formation from arginine useful for treating hypotension, inflammation, stroke and to restore vascular contractile sensitivity to the effects of .alpha..sub.1 adrenergic agonists are physiologically active compounds including N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties or monoalkyl carbon-substituted N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties, having the formula ##STR1## wherein R is (CH.sub.2).sub.y CH.sub.3 or H, R' is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, and R" is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, with y ranging from 0 to 5, and x is 0 or 1 and wherein none or only one of R, R' and R" provides an alkyl substituent on ornithine or lysine moiety, and wherein Q is a heme binding moiety and/or a sulfur-containing binding moiety and Q' is --NH.sub.2 when there is a double bond between the omega carbon and Q and Q' is .dbd.NH when there is a single bond between the omega carbon and Q, and physiologically acceptable acid addition salts thereof.

  阻止从精氨酸生成一氧化氮的抑制剂，用于治疗低血压，炎症，中风，并恢复血管对α1肾上腺素能激动剂的收缩敏感性的生理活性化合物，包括Nδ-取代鸟氨酸或Nε-取代赖氨酸基团或单烷基碳取代的Nδ-取代鸟氨酸或Nε-取代赖氨酸基团，其化学式为##STR1##其中R为（CH2）y CH3或H，R'为CH2或C（H）（CH2）y CH3，R"为CH2或C（H）（CH2）y CH3，y的范围为0至5，x为0或1，其中R、R'和R"中没有或只有一个在鸟氨酸或赖氨酸基团上提供烷基取代物，Q为血红素结合基团和/或含硫结合基团，Q'为-NH2，当ω碳和Q之间有双键时，Q'为.dbd.NH，当ω碳和Q之间有单键时，并且其生理上可接受的酸盐也包括在内。
• S-alkyl-isothioureido-amino acids and use thereof
  申请人：The Medical College of Wisconsin Research Foundation, Inc.

  公开号：US05364881A1

  公开（公告）日：1994-11-15

  Inhibitors of nitric oxide formation from arginine useful for treating hypotension, inflammation, stroke and to restore vascular contractile sensitivity to the effects of .alpha..sub.1 -adrenergic agonists are physiologically active compounds including N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties or monoalkyl carbon-substituted N.sup..delta. -substituted ornithine or N.sup..epsilon. -substituted lysine moieties, having the formula ##STR1## wherein R is (CH.sub.2).sub.y CH.sub.3 or H, R' is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, and R" is CH.sub.2 or C(H)(CH.sub.2).sub.y CH.sub.3, with y ranging from 0 to 5, and x is 0 or 1 and wherein none or only one of R, R' and R" provides an alkyl substituent on ornithine or lysine moiety, and wherein Q is alkyl having 1 to 5 carbon atoms, and physiologically acceptable acid addition salts thereof.

  阻断精氨酸向一氧化氮转化的抑制剂，可用于治疗低血压、炎症、中风以及恢复血管对α1-肾上腺素受体激动剂的收缩敏感性。这些生理活性化合物包括Nδ-取代鸟氨酸或Nε-取代赖氨酸基团或单烷基碳取代的Nδ-取代鸟氨酸或Nε-取代赖氨酸基团，其化学式为：其中R为(CH2)yCH3或H，R'为CH2或C(H)(CH2)yCH3，R"为CH2或C(H)(CH2)yCH3，y范围为0至5，x为0或1，其中R、R'和R"中没有或只有一个在鸟氨酸或赖氨酸基团上提供烷基取代基，Q为具有1至5个碳原子的烷基，以及其生理上可接受的酸盐。
• Synthesis and structural study of cyclic 5-aminovaleric acid-linked β-Ala–β-Ala dipeptides
  作者：Anne Mengel、Oliver Reiser、Jeffrey Aubé

  DOI：10.1016/j.bmcl.2008.07.082

  日期：2008.11

  5-Aminovaleric acid and ornithine were evaluated as linkers for the cyclization of beta-dipeptides. Two linked examples of beta-Ala-beta-Ala were prepared by standard coupling methods and their conformations probed by NMR, CD, and computational means. The data suggest that these non- or monosubstituted versions of the target compounds are flexible in solution. (C) 2008 Elsevier Ltd. All rights reserved.
• HEME BINDING COMPOUNDS AND USE THEREOF
  申请人：MEDICAL COLLEGE OF WISCONSIN RESEARCH FOUNDATION, INC.

  公开号：EP0707577A1

  公开（公告）日：1996-04-24