methyl L-valyl-L-leucinate | 54793-74-7

• 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: methyl L-valyl-L-leucinate
• 英文别名: H-Val-Leu-OMe；Val-Leu-OCH3；Val-Leu-OMe；Val-Leu-methylester；methyl (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-4-methylpentanoate
• CAS: 54793-74-7
• 化学式: C₁₂H₂₄N₂O₃
• mdl: MFCD26150341
• 分子量: 244.334
• InChiKey: NUJWVMIWMCEHGI-UWVGGRQHSA-N

物化性质

• 沸点：
  361.4±22.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl L-valyl-L-leucinate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以0.67 mmol的产率得到cyclo-Leu-Val
  参考文献：
  名称：

  Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (Theobroma cacao)

  摘要：

  The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and independent synthesis. Among these 25 compounds, 13 cis-configured diketopiperazines, namely, CYCIO(L-IIe-L-Phe), CYCIO(L-Val-L-Leu), CYCIO(L-Pro-L-Pro), CYCIO(L-IIe-L-Pro), CYCIO(L-Val-L-Tyr), CYCIO(L-Ala-L-Tyr), CYCIO(L-Phe-L-Ser), CYCIO(L-Ala-L-IIe), CYCIO(L-LeU-L-Phe), cyclo(L-Pro-L-Val), CYCIO(L-Pro-L-Thr), CYCIO(L-PrO-L-Tyr), and CYCIO(L-Val-L-Val) were identified for the first time in cocoa. In addition, the taste recognition thresholds for the metallic as well as the bitter taste of the diketopiperazines were determined, and after quantitative analysis by using two diastereomeric diketopiperazines as the internal standards, the sensory impact of the diketopiperazines was evaluated on the basis of their close-over-threshold (DoT) factors calculated as the ratio of the concentration and the threshold concentration of a compound. These data revealed DoT factors above 1.0 exclusively for cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Val-L-Leu), cis-cyclo(L-Ala-L-IIe), cis-cyclo(L-Ala-L-Leu), and cis-cyclo(L-IIe-L-Pro), whereas all of the other diketopiperazines were present below their individual bitter taste threshold concentrations and should therefore not contribute to the cocoa taste. Because the DoT factors do not consider the nonlinear relationship between the concentration and gustatory response of an individual compound, we, for the first time, report on the recording of dose/response functions describing the human bitter taste perception of diketopiperazines more precisely.

  DOI：

  10.1021/jf051313m
• 作为产物：
  描述：

  Z-Val-Leu-OH 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、500.0 kPa 条件下， 反应 24.5h， 生成 methyl L-valyl-L-leucinate
  参考文献：
  名称：

  Structures, Sensory Activity, and Dose/Response Functions of 2,5-Diketopiperazines in Roasted Cocoa Nibs (Theobroma cacao)

  摘要：

  The taste compounds inducing the blood-like, metallic bitter taste sensation reported recently for a dichloromethane extract prepared from roasted cocoa nibs were identified as a series of 25 diketopiperazines by means of HPLC degustation, LC-MS/MS, and independent synthesis. Among these 25 compounds, 13 cis-configured diketopiperazines, namely, CYCIO(L-IIe-L-Phe), CYCIO(L-Val-L-Leu), CYCIO(L-Pro-L-Pro), CYCIO(L-IIe-L-Pro), CYCIO(L-Val-L-Tyr), CYCIO(L-Ala-L-Tyr), CYCIO(L-Phe-L-Ser), CYCIO(L-Ala-L-IIe), CYCIO(L-LeU-L-Phe), cyclo(L-Pro-L-Val), CYCIO(L-Pro-L-Thr), CYCIO(L-PrO-L-Tyr), and CYCIO(L-Val-L-Val) were identified for the first time in cocoa. In addition, the taste recognition thresholds for the metallic as well as the bitter taste of the diketopiperazines were determined, and after quantitative analysis by using two diastereomeric diketopiperazines as the internal standards, the sensory impact of the diketopiperazines was evaluated on the basis of their close-over-threshold (DoT) factors calculated as the ratio of the concentration and the threshold concentration of a compound. These data revealed DoT factors above 1.0 exclusively for cis-cyclo(L-Pro-L-Val), cis-cyclo(L-Val-L-Leu), cis-cyclo(L-Ala-L-IIe), cis-cyclo(L-Ala-L-Leu), and cis-cyclo(L-IIe-L-Pro), whereas all of the other diketopiperazines were present below their individual bitter taste threshold concentrations and should therefore not contribute to the cocoa taste. Because the DoT factors do not consider the nonlinear relationship between the concentration and gustatory response of an individual compound, we, for the first time, report on the recording of dose/response functions describing the human bitter taste perception of diketopiperazines more precisely.

  DOI：

  10.1021/jf051313m

文献信息

• A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
  作者：Sandip V. Jadhav、Anupam Bandyopadhyay、Sushil N. Benke、Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1039/c0ob01226b

  日期：——

  for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals

  一种简便，高效且无外消旋的方法，使用该方法合成N保护的β-氨基醇和肽醇N-羟基琥珀酰亚胺描述了活性酯。使用这种方法，可以高产率分离出二肽，三肽和五肽醇。分析了β-氨基醇，二肽和三肽醇的晶体构象，在三肽醇晶体中观察到了明确定义的III型β角。发现该方法与Fmoc-，Boc-和其他侧链保护基相容。
• Synthesis of the nonatetracontapeptide corresponding to the entire amino acid sequence of thymopoietin III and its effect on the impaired T-lymphocyte transformation of a patient with common variable immunodeficiency.
  作者：TAKASHI ABIKO、HIROSHI SHISHIDO、HIROSHI SEKINO

  DOI：10.1248/cpb.34.2133

  日期：——

  The nonatetracontapeptide corresponding to the entire amino acid sequence of thymopoietin III was synthesized by assembling ten peptide fragments in solution followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole (molar ratio, 1 : 1) in trifluoroacetic acid in the presence of m-cresol. The synthetic nonatetracontapeptide was tested for effect on impaired T-lymphocyte transformation by phytohemagglutinin (PHA) in common variable immunodeficiency.The synthetic nonatetracontapeptide was found to have restorin activity on the T-lymphocyte transformation by PHA. However, the restoring activity of the synthetic nonatetracontapeptide was lower than that of the synthetic thymopoietin I at a dos of 2 μg/ml.

  对应于胸腺生成素III整个氨基酸序列的非九十三肽，是通过溶液中组装十个肽片段，随后在间甲酚存在下用1M三氟甲磺酸-噻吩甲烷（摩尔比，1:1）在三氟乙酸中脱保护来合成的。合成的非九十三肽被测试了其在常见变异性免疫缺陷中对植物血凝素（PHA）诱导的受损T淋巴细胞转化的影响。发现合成的非九十三肽对PHA诱导的T淋巴细胞转化具有恢复活性。然而，合成的非九十三肽的恢复活性在2μg/ml剂量下低于合成胸腺生成素I的活性。
• Inhibition of cathepsin D by substrate analogs containing statine and by analogs of pepstatin
  作者：Nirankar S. Agarwal、Daniel H. Rich

  DOI：10.1021/jm00162a015

  日期：1986.12

  -Val-Leu-OR, with statine [3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid, Sta) or with Sta-Phe. The best inhibitor, Boc-Phe-Leu-Ala-(S,S)-Sta-Val-Leu-OMe, inhibited cathepsin D with a Ki value of 1.1 nM. In general, the more effective inhibitors were consistent with the proposal that statine functions as a replacement for a dipeptidyl unit. Thirty-five known pepstatin analogues also were evaluated

  合成了五种新的组织蛋白酶D抑制剂并将其作为牛组织蛋白酶D的抑制剂进行测试。这些化合物是通过替换良好的组织蛋白酶D底物Boc-Phe-Leu-Ala-Phe-Phe-Val-Leu的Phe-Phe二肽基单元而衍生的。 -OR，与他汀[3S，4S）-4-氨基-3-羟基-6-甲基庚酸（Sta）或与Sta-Phe。最好的抑制剂Boc-Phe-Leu-Ala-（S，S）-Sta-Val-Leu-OMe抑制组织蛋白酶D，Ki值为1.1 nM。通常，更有效的抑制剂与他汀类药物作为二肽基单位的替代品的提议是一致的。还评估了三十五个已知的胃抑素类似物作为组织蛋白酶D抑制剂。P4和P3'位置的取代基对于最大限度抑制这种天冬氨酸蛋白酶很重要，
• Application of carbodiimide mediated Lossen rearrangement for the synthesis of α-ureidopeptides and peptidyl ureas employing N-urethane α-amino/peptidyl hydroxamic acids
  作者：N. Narendra、Gundala Chennakrishnareddy、Vommina V. Sureshbabu

  DOI：10.1039/b905790k

  日期：——

  Application of the Lossen rearrangement to the synthesis of N-urethane protected α-peptidyl ureas and ureidopeptides is reported. The carbodiimide mediated rearrangement of N-Boc/Z/Fmoc protected α-amino/peptide hydroxamic acids into isocyanates and coupling of the latter with the amino acid esters/peptide esters have been accomplished in a single-pot to obtain good yields of urea products. Synthesis

  报道了Lossen重排在N-氨基甲酸酯保护的α-肽基脲和脲肽的合成中的应用。这碳二亚胺N- Boc / Z / Fmoc保护的α-氨基/肽异羟肟酸介导的重排成异氰酸酯，后者与氨基酸酯/肽酯的偶联已在单罐中完成，从而获得了较高的收率。尿素产品。还已经使用相同的方法经由N-保护的天冬氨酸的异羟肟酸酯衍生物合成脲基丙氨酸衍生物。
• N-amination using N-methoxycarbonyl-3-phenyloxaziridine. Direct access to chiral N_β-protected α-hydrazinoacids and carbazates
  作者：Joëlle Vidal、Jacques Drouin、André Collet

  DOI：10.1039/c39910000435

  日期：——

  Primary and secondary amines N–H, including α-aminoacids, can be converted under mild conditions to the corresponding carbazates N–NH–CO2Me, on reaction with N-methoxycarbonyl-3-phenyloxaziridine 1.

  初级和次级胺的 N–H，包括 α-氨基酸，可以在温和条件下与 N-甲氧基碳酰基-3-苯基呋喃啶 1 反应，转化为相应的脲体 N–NH–CO2Me。