N-BOC-4-氨基-3-甲基-丁酸 | 259857-57-3

• 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
• 中文名称: N-BOC-4-氨基-3-甲基-丁酸
• 中文别名: (3R)-3-甲基-4-({[(2-甲基-2-丙基)氧基]羰基}氨基)丁酸
• 英文名称: (R)-(+)-4-(tert-butoxycarbonyl)amino-3-methylbutanoic acid
• 英文别名: (3R)-4-{[(tert-butoxy)carbonyl]amino}-3-methylbutanoic acid；(3R)-3-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 259857-57-3
• 化学式: C₁₀H₁₉NO₄
• 分子量: 217.265
• InChiKey: FNYRVJJDNPAVSS-SSDOTTSWSA-N

物化性质

• 沸点：
  363.2±25.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-BOC-4-氨基-3-甲基-丁酸 在 C₅H₁₁NSi 作用下， 以 正己烷 、 甲苯 为溶剂， 以71%的产率得到(R)-(-)-methyl 4-(tert-butoxycarbonyl)amino-3-methylbutanoate
  参考文献：
  名称：

  取代基和氨基位置对 γ-氨基酯的脂肪酶催化拆分的影响：一项揭示南极假丝酵母脂肪酶 B 对映选择性的分子对接研究

  摘要：

  与N保护的 β 3氨基酯相比，南极念珠菌脂肪酶 B 催化的氨基酯的动力学拆分具有 α ( γ 2 )、β ( γ 3 ) 和 γ ( γ 4 ) 立体中心，在催化腔的高度。分子对接研究有助于确定空间排斥区域涉及 Ile189 和 Val190 残基以及氨基键合区域，其中有利于与 Asp134 残基的氢键。

  DOI：

  10.1002/ejoc.202100712
• 作为产物：
  描述：

  (R)-(+)-4-methylpyrrolidin-2-one 在 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-BOC-4-氨基-3-甲基-丁酸
  参考文献：
  名称：

  Enantioselective Preparation of γ ‐Amino Acids and γ ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary

  摘要：

  DOI：

  10.1002/(sici)1522-2675(19991215)82:12<2365::aid-hlca2365>3.0.co;2-#

文献信息

• γ2-,γ3-, andγ2,3,4-Amino Acids, Coupling toγ-Hexapeptides: CD Spectra, NMR Solution and X-ray Crystal Structures ofγ-Peptides
  作者：Dieter Seebach、Meinrad Brenner、Magnus Rueping、Bernhard Jaun

  DOI：10.1002/1521-3765(20020201)8:3<573::aid-chem573>3.0.co;2-h

  日期：2002.2.1

  There are numerous possible gamma-amino acids with different degrees of substitution and with various constitutions and configurations. Of these the gamma(4)-and the like- and unlike-gamma(2.4)-amino acids have been previously used as building blocks in gamma-peptides. The synthesis of gamma(2)-, gamma(3)-, and gamma(2.3.4) peptides is now described. The corresponding amino acids have been prepared by Michael addition of chiral N-acyl-oxazolidinone enolates to nitro-olefins, with subsequent reduction of the NO2 to NH2 groups. Such additions to E-2-methyl-nitropropene provide (2R,3R,4R)-2-alkyl-3-methyl-4amino-pentanoic acid derivatives (9, 10, 11). Stepwise coupling and fragment coupling lead to gamma-di-, tri-, and hexapeptides (12-23), which were fully characterized. The crystal structures of one of the gamma-amino acids (2,3-dimethyl-4-amino-pentanoic acid .HCl, 9 a), of a gamma(2.3.4)-di- and a gamma(2.3.4)-tetrapeptide (20, 22) are described, and the NMR solution structure in MeOH of a gamma(2.3.4)-hexapeptide (3) has been determined (using TOCSY, COSY, HSQC, HMBC and ROESY measurements and a molecular dynamics simulated-annealing protocol). A linear conformation (sheet-like), a novel (M) helix built of nine-membered hydrogen-bonded rings, and (M) 2.6(14) helices have thus been identified. NMR measurements at different temperatures (298-393 K) and H/D-exchange rates obtained for the y(2.3.4)- -hexapeptide are interpreted as evidence for the stability of the 2.6(14) helix (no "melting") and for its non-cooperative folding mechanism. CD Spectra of the gamma-peptides have been measured in MeOH and CH3CN, indicating that only the protected and unprotected y(2.3.4)-hexapeptide is present as the 2.614 helix in solution. The structures of the gamma(2)- and gamma(3)-hexapeptides (1, 2) could not be determined.
• [EN] NOVEL DIPEPTIDYL PEPTIDASE-IV INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE LA DIPEPTIDYL PEPTIDASE IV
  申请人：LG LIFE SCIENCES LTD

  公开号：WO2008093960A1

  公开（公告）日：2008-08-07

  [EN] The present invention relates to novel compounds exhibiting excellent inhibitory activity versus Dipeptidyl Peptidase-IV (DPP-IV), methods of preparing the same and pharmaceutical compositions containing the same as an active agent.
  [FR] La présente invention concerne de nouveaux composés présentant une excellente activité inhibitrice vis-à-vis de la dipeptidyl peptidase IV (DPP IV), ainsi que des procédés de préparation de ces composés et des compositions pharmaceutiques contenant lesdits composés comme agent actif.
• Enantioselective Preparation of <i>γ</i> ‐Amino Acids and <i>γ</i> ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary
  作者：Meinrad Brenner、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2365::aid-hlca2365>3.0.co;2-#

  日期：1999.12.15
• Effect of the Substituent and Amino Group Position on the Lipase‐Catalyzed Resolution of γ‐Amino Esters: A Molecular Docking Study Shedding Light on<i>Candida antarctica</i>lipase B Enantioselectivity
  作者：Marina A. Ortega‐Rojas、Edmundo Castillo、Rodrigo Said Razo‐Hernández、Nina Pastor、Eusebio Juaristi、Jaime Escalante

  DOI：10.1002/ejoc.202100712

  日期：2021.9.14

  In contrast to N-protected β3-amino esters, the Candida antarctica lipase B catalyzed kinetic resolution of amino esters holding alpha (γ2), beta (γ3), and gamma (γ4) stereocenters is strongly compromised by steric factors at the level of the catalytic cavity. Molecular docking studies helped establish that the steric exclusion region involves the Ile189 and Val190 residues and the amino bonding region

  与N保护的 β 3氨基酯相比，南极念珠菌脂肪酶 B 催化的氨基酯的动力学拆分具有 α ( γ 2 )、β ( γ 3 ) 和 γ ( γ 4 ) 立体中心，在催化腔的高度。分子对接研究有助于确定空间排斥区域涉及 Ile189 和 Val190 残基以及氨基键合区域，其中有利于与 Asp134 残基的氢键。