(S)-2-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-methylbutanoic acid | 259857-55-1

• 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: (S)-2-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-methylbutanoic acid
• 英文别名: (2S)-3-methyl-2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]butanoic acid
• CAS: 259857-55-1
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: WQZNLPWJNZRMIZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (S)-2-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-methylbutanoic acid 、 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 为溶剂， 以1.05 g的产率得到Boc-γ²hhVal-γ²hhAla-γ²hhLeu-OBn
  参考文献：
  名称：

  γ2-,γ3-, andγ2,3,4-Amino Acids, Coupling toγ-Hexapeptides: CD Spectra, NMR Solution and X-ray Crystal Structures ofγ-Peptides

  摘要：

  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.

  DOI：

  10.1002/1521-3765(20020201)8:3<573::aid-chem573>3.0.co;2-h
• 作为产物：
  描述：

  (S)-4-isopropyl-3-[(S)-3-methyl-2(2-nitroethyl)butanoyl]-5,5-diphenyloxazolidin-2-one 在 镍 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 21.0h， 生成 (S)-2-{2-[(tert-butoxycarbonyl)amino]ethyl}-3-methylbutanoic acid
  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

• Determination of Enantiomer Purity ofβ- andγ-Amino Acids by NMR Analysis of Diastereoisomeric Palladium Complexes
  作者：Andreas Böhm、Dieter Seebach

  DOI：10.1002/1522-2675(20001220)83:12<3262::aid-hlca3262>3.0.co;2-p

  日期：2000.12.20

  Like alpha -amino acids, beta- and gamma -amino acids form spirobicyclic complexes (see 2 and 3) by reaction with the chiral di-mu -chlorobis2-[1-dimethylamino-xN)-ethyl]phenyl-xC}dipalladium complexes 1 under basic conditions (Scheme 1 and X-ray structures in Fig. I). The diastereoisomeric complexes formed with mixtures of enantiomers of either the amino acids or the dichloro-dipalladium complexes give rise to marked chemical-shift differences in the H-1- and C-13-NMR spectra (Figs. 2-4) to allow determination of the enantiomer purities. A simple procedure is described by which beta- and gamma -amino acids (which may be generated in situ from Boc- or Fmoc-protected precursors) are converted to the Pd complexes and subjected to NMR measurements. The effects of solvent, temperature, and variation of the aryl group in the chiral derivatizing Pd reagent are described (Figs. 4 and 5). The methyl esters of B-amino acids can also be employed, forming diastereoisomeric chloro[(amino-xN)aryl-xC][(amino-xN)alkanoate]palladium complexes 6 for determining enantiomer ratios (Scheme 6). The new method has great scope, as demonstrated for beta (2)-, beta (3), beta (2,3)-, beta (2,2,3)-, gamma (2)-, gamma (3)-, gamma (4)-, and gamma (2,3,4)- amino acid derivatives.
• β- and γ-Di- and Tripeptides as Potential Substrates for the Oligopeptide Transporter hPepT1
  作者：Ina Hubatsch、Per I. Arvidsson、Dieter Seebach、Kristina Luthman、Per Artursson

  DOI：10.1021/jm070148u

  日期：2007.10.1

  The hPepT1-mediated transport properties of a series of 11 synthesized beta- and gamma-peptides have been studied in Caco-2 cells. The results show that several of the compounds interact with the peptide transporter, but only two beta-dipeptides act as substrates and are transported across the cell monolayers. These two are less-efficient substrates than alpha-peptides. Larger derivatives than beta-dipeptides do not act as hPepT1 substrates, but instead, they appear to be substrates for P-glycoprotein efflux.