N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester | 76944-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester
• 英文别名: 2,5-Dioxopyrrolidin-1-yl 5-(((benzyloxy)carbonyl)amino)pentanoate；(2,5-dioxopyrrolidin-1-yl) 5-(phenylmethoxycarbonylamino)pentanoate
• CAS: 76944-94-0
• 化学式: C₁₇H₂₀N₂O₆
• 分子量: 348.356
• InChiKey: ZCXCQSIWRSUSQZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102.01
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙二醇甲醚 、 水 、 溶剂黄146 、 丙酮 为溶剂， 80.0 ℃ 、275.79 kPa 条件下， 反应 13.0h， 生成 monosodium mono(((2R,3S,4R,5R)-3,4-dihydroxy-5-(6-((5-((4-(5-(2-iodoacetamido)-N-methylpentanamido)butyl)(methyl)amino)-5-oxopentyl)amino)-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl triphosphate)
  参考文献：
  名称：

  Use of adenine nucleotide derivatives to assess the potential of exo-active-site-directed reagents as species- or isozyme-specific enzyme inactivators. 3. Synthesis of adenosine 5'-triphosphate derivatives with N6- or 8-substituents bearing iodoacetyl groups

  摘要：

  Several series of N6- or 8-substituted derivatives of adenosine 5'-triphosphate (ATP) were synthesized. N6-(omega-Aminoalkyl) derivatives of adenosine 5'-monophosphate (AMP) were converted into their omega-N-carbobenzyloxy derivatives, and these were converted, via the 2',3'-O-carbonyl derivatives of their 5'-phosphorimidazolidates, into the corresponding ATP derivatives. Hydrogenolytic removal of the carbobenzyloxy groups, followed by iodoacetylation of the omega-amino groups with N-(iodoacetoxy)succinimide, gave N6-R-ATP, where R = (CH2)nNHCOCH2I (n = 2--8) or (CH2)nCON)CH3)(CH2)mN(CH3)CO(CH2)nNHCOCH2I (n = m = 3; n = 3, m = 4; n = 4, m = 3; n = m = 4). Condensation of N6-(omega-aminoalkyl) derivatives of AMP with N-hydroxysuccinimide esters of omega-[N-(carbobenzyloxy)amino] carboxylic acids gave N6-(CH2)nNHCO(CH2)mNH-Cbz derivatives of AMP which, upon conversion to the corresponding derivatives of ATP, followed by removal of the carbobenzyloxy group and iodoacetylation, as described above, gave N6-(CH2)nNHCO(CH2)mNHCOCH2I-ATP derivatives (n = 3, m = 5 or 6; n = 4, m = 5; n = 6, m = 1--6). The same sequence of reactions starting with N6-[omega-(methylamino)alkyl] derivatives of N6-CH3-AMP gave N6-CH3, N6-(CH2)nH(CH3)CO(CH2)mNHCOCH2I derivatives of ATP (n = 4, m = 3, 5 or 6; n = 6, m = 5 or 6). Reaction of alpha, omega-diaminoalkanes with 8-Br-ATP gave 8-NH(CH2)nNH2 derivatives of ATP, which upon iodoacetylation gave 8-NH(CH2)nNHCOCH2I derivatives of ATP (n = 2, 4, 6, or 8). Substrate and inhibitor properties indicated that the ATP derivatives are potential exco-ATP-site-directed inactivators of hexokinases, adenylate kinases, and pyruvate kinases.

  DOI：

  10.1021/jm00346a009
• 作为产物：
  描述：

  氯甲酸苄酯 在 吡啶 作用下， 生成 N-benzyloxycarbonyl-5-aminovaleric acid succinimide ester
  参考文献：
  名称：

  Ogura, Haruo; Takeda, Kazuyoshi, Heterocycles, 1981, vol. 15, # 1, p. 467 - 468

  摘要：

  DOI：

文献信息

• Bridged isocytosine-adenosine compounds: Synthesis and antibacterial evaluation
  作者：O. William Lever、B. Randall Vestal

  DOI：10.1002/jhet.5570230348

  日期：1986.5

  In an approach to novel antibacterial agents, we synthesized a series of 5-nitrosoisocytosines in which a 6-alkylamino substituent is bridged, through an amide linkage at the terminus of the alkyl chain, to the 5′-position of a 5′-deoxyadenosine moiety. A corresponding series of 5-nitro analogues were also prepared. None of the bridged compounds showed significant antibacterial activity.

  在一种新型抗菌剂的方法中，我们合成了一系列5-亚硝基异胞嘧啶，其中6-烷基氨基取代基通过烷基链末端的酰胺键桥接至5'-脱氧腺苷的5'-位部分。还制备了相应的5-硝基类似物系列。没有一种桥接化合物显示出明显的抗菌活性。
• Inhibitors of Tripeptidyl Peptidase II. 2. Generation of the First Novel Lead Inhibitor of Cholecystokinin-8-Inactivating Peptidase:  A Strategy for the Design of Peptidase Inhibitors
  作者：C. Robin Ganellin、Paul B. Bishop、Ramesh B. Bambal、Suzanne M. T. Chan、James K. Law、Benoit Marabout、Pratibha Mehta Luthra、Andrew N. J. Moore、Olivier Peschard、Pierre Bourgeat、Christiane Rose、Froylan Vargas、Jean-Charles Schwartz

  DOI：10.1021/jm990226g

  日期：2000.2.1

  fluorimetric assay based on the hydrolysis of the artificial substrate Ala-Ala-Phe-amidomethylcoumarin. A series of di- and tripeptides having various alkyl or aryl side chains was studied to determine the accessible volume for binding and to probe the potential for hydrophobic interactions. From this initial study the tripeptides Ile-Pro-Ile-OH (K(i) = 1 microM) and Ala-Pro-Ala-OH (K(i) = 3 microM) and dipeptide

  失活胆囊收缩素8（CCK-8）的肽酶是一种丝氨酸肽酶，已证明是三肽基肽酶II的膜结合同工型（EC 3.4.14.10）。它在Met-Gly键处裂解神经递质CCK-8硫酸盐，得到Asp-Tyr（SO（3）H）-Met-OH + Gly-Trp-Met-Asp-Phe-NH（2）。为了寻找该肽酶的可逆抑制剂，使用基于人工底物Ala-Ala-Phe-酰胺基甲基香豆素水解的荧光分析法来表征酶促结合亚位点。对具有各种烷基或芳基侧链的一系列二肽和三肽进行了研究，以确定可结合的体积并探讨疏水相互作用的可能性。根据这项初步研究，三肽Ile-Pro-Ile-OH（K（i）= 1 microM）和Ala-Pro-Ala-OH（K（i）= 3 microM）和二肽酰胺Val-Nvl-NHBu（K（ i）= 3 microM）作为线索出现。这些结构的比较导致Val-Pro-NHBu（K（i）= 0.57 micr
• PRESTON R. K.; BELVEDERE J. F.; SCHWARTZ J., INST. CANCER RES. SCI. REPT., 1976-1977, NO 22, 216-219
  作者：PRESTON R. K.、 BELVEDERE J. F.、 SCHWARTZ J.

  DOI：——

  日期：——
• OGURA HARUO; TAKEDA KAZUYOSHI, HETEROCYCLES, 1981, 15, NO 1, SPEC. ISSUE, 467-468
  作者：OGURA HARUO、 TAKEDA KAZUYOSHI

  DOI：——

  日期：——