Boc-Val-Gly-OEt | 4526-92-5

• 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: Boc-Val-Gly-OEt
• 英文别名: ethyl (tert-butoxycarbonyl)-L-valylglycinate；ethyl 2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]acetate
• CAS: 4526-92-5
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: FJMIIVRCQWRALB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  Boc-Val-Gly-OEt 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 BOC-缬氨酰-甘氨酸
  参考文献：
  名称：

  Inhibition of human leukocyte elastase (HLE) by N-substituted peptidyl trifluoromethyl ketones

  摘要：

  A series of tripeptides possessing trifluoromethyl or aryl ketone residues at P1 were prepared and evaluated both in vitro and in vivo as potential inhibitors of human leukocyte elastase (HLE). Tripeptides containing non naturally occurring N-substituted glycine residues at the P2-position have been demonstrated to be potent in vitro inhibitors of HLE, with IC50 values in the submicromolar range. Sterically demanding substituents on the P2-nitrogen have no detrimental effect on in vitro potency. The inhibition process presumably acts via hemiketal formation with the active site Ser195 of HLE, and is facilitated by the strongly electron withdrawing trifluoromethyl functionality. Deletion of the amino acid at the P3-subsite region affords inactive compounds. Valine is the preferred residue at the P1-position, whereas the corresponding glycine, alanine, alpha,alpha-dimethylglycine, or phenylalanine analogues are all inactive. The compounds described herein all confer a high degree of in vitro specificity when tested against representative cysteine, aspartyl, metallo, and other serine proteases. One of the most potent in vitro inhibitors is (3RS)-N-[4-[[[(4-chlorophenyl)sulfonyl]amino]carbonyl]phenyl]oxomethyl]-L-valyl-N-(2,3-dihydro-1H-inden-2-yl)glycine N-[3-(1,1,1-trifluoro-4-methyl-2-oxopentyl)]amide (20i; BI-RA-260) (IC50 = 0.084-mu-M). Compound 20i was also tested in hamsters in an elastase-induced pulmonary hemorrhage (EPH) model. In this model, intratracheal (it.) administration of 20i, 5 min prior to HLE challenge, effectively inhibited hemorrhage in a dose-dependent manner with an ED50 of 4.8-mu-g. The inhibitor 20i, 20-mu-g administered it. 24, 48, and 72 h prior to HLE challenge, exhibits significant inhibition against hemorrhage at all time points (97%, 64% and 49%, respectively). In a 21-day chronic model of emphysema in hamsters, 200-mu-g of HLE administered it. caused an elastase-induced emphysema in the lungs which can be quantitated histologically utilizing image analysis. In this assay, 20i significantly inhibited pulmonary lesions associated with septal destruction and increased alveolar spaces, when dosed at 20-mu-g it. 5 min prior to challenge with HLE.

  DOI：

  10.1021/jm00082a005
• 作为产物：
  描述：

  N-Boc-L-缬氨酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Boc-Val-Gly-OEt
  参考文献：
  名称：

  Shimagaki, Masayuki; Koshiji, Hiroko; Oishi, Takeshi, Phosphorus and Sulfur and the Related Elements, 1983, vol. 16, p. 45 - 58

  摘要：

  DOI：

文献信息

• Synthesis of the heptadecapeptide corresponding to the entire amino acid sequence of salmon melanin-concentrating hormone (MCH).
  作者：KENJI OKAMOTO、KOICHI YASUMURA、KAZUYOSHI FUJITANI、YOSHIAKI KISO、HIROSHI KAWAUCHI、ICHIRO KAWAZOE、HARUAKI YAJIMA

  DOI：10.1248/cpb.32.2963

  日期：——

  The heptadecapeptide corresponding to the entire amino acid sequence of melaninconcentrating hormone (MCH), isolated from chum salmon pituitaries, was synthesized by successive condensation of four peptide fragments and the N-terminal amino acid, i. e., Boc-(14-17)-OBzl, Boc-(9-13)-OH, Boc-(5-8)-NHNH2, Boc-(2-4)-NHNH2 and Boc-Asp (OBzl)-OH, followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid (TFA) and disulfide formation through the S-sulfonate. When melanin-concentrating activity was measured on a tilapia scale, the minimum effective concentration of the synthetic peptide was equivalent to that of natural salmon MCH (1nM).

  从大麻哈鱼脑下垂体中分离出的、与促黑激素（MCH）整个氨基酸序列相对应的十七肽，是通过四个肽片段和N-端氨基酸，即Boc-(14-17)-OBzl、Boc-(9-13)-OH、Boc-(5-8)-NHNH2、Boc-(2-4)-NHNH2 和Boc-Asp(OBzl)-OH，依次缩合合成，随后用三氟乙酸（TFA）中的1M三氟甲磺酸-硫茴处理，通过S-磺酸酯形成二硫键并去保护。当在罗非鱼身上测量促黑活性时，合成肽的最小有效浓度与天然大麻哈鱼MCH的浓度（1nM）相当。
• Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
  作者：Pilar Cledera、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(98)00744-3

  日期：1998.10

  4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (2) was studied. Four synthetic methods were compared, namely direct condensation with the product of the reaction between anthranilic acid and thionyl chloride, transformation into monothioiminoethers or monoiminoethers followed by reaction with anthranilic acid derivatives, and monoacylation with o-azidobenzoyl chloride followed by intramolecular aza-Wittig reaction

  研究了3-芳基亚甲基哌嗪-2，5-二酮（1）向1-芳基亚甲基-2，4-二氢-1 H-吡嗪并[ 2，1 - b ]喹唑啉-3，6-二酮（2）的转化。比较了四种合成方法，即直接与邻氨基苯甲酸和亚硫酰氯之间的反应产物缩合，转化为单硫亚氨基醚或单亚氨基醚，然后与邻氨基苯甲酸衍生物反应，与邻叠氮基苯甲酰氯单酰化，然后进行分子内aza-Wittig反应。通过后一种方法可获得最佳结果。
• A novel reagent (N_succinimidyl diphenylphosphate) for synthesis of active ester and peptide
  作者：Haruo Ogura、Sachiko Nagai、Kazuyoshi Takeda

  DOI：10.1016/s0040-4039(00)92747-3

  日期：——

  N-succinimidyl diphenylphosphate (SDPP) was prepared. This reagent was useful for the preparation of active esters and peptides in stead of dicyclohexylcarbodiimide.

  制备了N-琥珀酰亚胺基二苯基磷酸酯（SDPP）。该试剂可用于制备活性酯和肽，而不是二环己基碳二亚胺。
• Microwave-Assisted Synthesis of 2,5-Piperazinediones under Solvent-Free Conditions
  作者：J. Carlos Menéndez、Alberto López-Cobeñas、Pilar Cledera、J. Domingo Sánchez、Pilar López-Alvarado、M. Teresa Ramos、Carmen Avendaño

  DOI：10.1055/s-2005-918473

  日期：——

  A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters.

  描述了一种合成 2,5-哌嗪二酮的通用、高效和环保的方法，包括 N-Boc 二肽酯的微波辐射。
• Stimulus Responsive Behavior of Elastin-Based Side Chain Polymers
  作者：Lee Ayres、Kaspar Koch、P. Hans H. M. Adams, and、Jan C. M. van Hest

  DOI：10.1021/ma047923p

  日期：2005.3.1

  this series of elastin based side chain block copolymers was investigated by changing the degree of polymerization, polymer concentration, and pH. The effects of these parameters on the LCST of the side chain block copolymers were similar when compared with linear poly(VPGVG). The aggregates which were formed above the transition temperature were investigated using light scattering and cryo-SEM techniques

  多年来，线性聚（VPGVG）作为结构蛋白弹性蛋白的模型已被广泛研究。弹性蛋白的特征在于较低的临界溶液温度（LCST）。该LCST可能受几个因素的影响，主要是分子量，浓度和pH值。使用原子转移自由基聚合（ATRP）合成ABA型嵌段共聚物，其中VPGVG序列位于A嵌段的侧链中，而B嵌段为聚乙二醇（PEG）。通过改变聚合度，聚合物浓度和pH值，研究了这一系列基于弹性蛋白的侧链嵌段共聚物的LCST行为。与线性聚（VPGVG）相比，这些参数对侧链嵌段共聚物的LCST的影响是相似的。