perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate | 50903-47-4

• 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: perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate
• 英文别名: Boc-Gly-OPfp；Penta-fluorophenyl boc-glycinate；(2,3,4,5,6-pentafluorophenyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 50903-47-4
• 化学式: C₁₃H₁₂F₅NO₄
• 分子量: 341.235
• InChiKey: CSJYMJMVFOPPHL-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  372.7±42.0 °C(Predicted)
• 密度：
  1.404±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate 在 水 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 BOC-甘氨酸
  参考文献：
  名称：

  Girin, S. K.; Shvachkin, Yu. P., Journal of general chemistry of the USSR, 1983, vol. 53, # 10, p. 2138 - 2142

  摘要：

  DOI：
• 作为产物：
  描述：

  五氟苯酚 在 吡啶 、 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 perfluorophenyl 2-((tert-butoxycarbonyl)amino)acetate
  参考文献：
  名称：

  Bis(pentaluorophenyl) sulfite ? A new reagent for the synthesis of activated pentafluorophenyl esters of N-protected amino acids

  摘要：

  DOI：

  10.1007/bf00952635

文献信息

• Carboxylated Glucuronic Poly-amido-saccharides as Protein Stabilizing Agents
  作者：Sarah E. Stidham、Stacy L. Chin、Eric L. Dane、Mark W. Grinstaff

  DOI：10.1021/ja5036804

  日期：2014.7.9

  (PASs). To investigate the effect of adding ionizable carboxylic acid groups, such as those found in natural polysaccharides containing glucuronic acid, the oxidation of the primary alcohol at the C6-position of the repeat unit to a carboxylic acid is reported. TEMPO-mediated oxidation provides control over the degree of oxidation in excellent yield. Based on circular dichroism, the oxidized polymers possess

  新型碳水化合物基聚合物的合成允许在单体水平上针对特定性质调整结构，并将可用结构的范围扩展到自然界中发现的结构之外。使用受控的阴离子聚合，合成了一种新型碳水化合物聚合物，其中葡萄糖衍生的单体通过 α-1,2 酰胺键连接，得到对映体纯聚酰胺糖 (PAS)。为了研究添加可电离的羧酸基团的影响，例如在含有葡萄糖醛酸的天然多糖中发现的那些，报道了重复单元 C6 位伯醇氧化为羧酸。TEMPO 介导的氧化以优异的产率控制氧化程度。基于圆二色性，氧化的聚合物在水溶液中具有有序的螺旋二级结构。最后，氧化的 PAS 比目前广泛使用的蛋白质稳定剂海藻糖更能稳定溶菌酶以应对脱水和冷冻应激。
• Monofunctional electrophilic and nucleophilic derivatives of meso-tetraphenylporphyrin for attachment to peptides
  作者：Susan E. Matthews、Colin W. Pouton、Michael D. Threadgill

  DOI：10.1039/c39950001809

  日期：——

  4-Nitrophenyl N-[4-(10,15,20-triphenylporphyrin-5-yl)phenyl]carbamate and 5-[4-(N-glycylamino)phenyl]-10,15,20-triphenylporphyrin have been synthesised from a readily prepared monofunctionalised porphyrin; they couple efficiently with the side-chains of extended lysyl and glutamyl peptide derivatives, respectively.

  4-硝基苯基N-[4-(10,15,20-三苯基卟啉-5-基)苯基]氨基甲酸酯和5-[4-(N-甘氨酰氨基)苯基]-10,15,20-三苯基卟啉已从易于制备的单功能化卟啉合成得到。它们分别能高效地与延伸的赖氨酰和谷氨酰肽衍生物的侧链结合。
• DIPEPTIDE MIMETICS OF NGF AND BDNF NEUROTROPHINS
  申请人：Seredenin Sergey Borisovich

  公开号：US20110312895A1

  公开（公告）日：2011-12-22

  The invention relates to compounds having either agonist or antagonist activities for the neurotrophins NGF and BDNF and represented by monomeric or dimeric substituted dipeptides that are analogs of the exposed portions of loop 1 or loop 4 regions of these neurotrophins near or at a beta-turn of the respective loop. N-acylated substituents of these dipeptides are biostereoisomers of the amino acid residues preceding these dipeptide sequences in the neurotrophin primary structure. The dimeric structure is produced advantageously by using hexamethylenediamine to which dipeptides are attached via their carboxyl groups. The claimed compounds displayed neuroprotective and differentiation-inducing activities in cellular models and enhanced the amount of phosphorylated tyrosine kinase A and the heat shock proteins Hsp32 and Hsp70 in the concentration range of 10 −9 to 10 −5 M. They also displayed neuroprotective, anti-parkinsonian, anti-stroke, anti-ischemic, anti-depressant and anti-amnestic activities in animal models and were active in experimental models of Alzheimer's disease. These in vivo effects of the claimed compounds are displayed in the dose range of 0.01 to 10 mg/kg when administered intraperitoneally.

  该发明涉及具有神经营养因子NGF和BDNF的激动剂或拮抗剂活性的化合物，这些化合物由单体或二聚体取代二肽代表，这些二肽代表这些神经营养因子的环1或环4区域的暴露部分的类似物，靠近或在各自环的β-转弯处。这些二肽的N-酰化取代物是神经营养因子原始结构中这些二肽序列之前的氨基酸残基的生物立体异构体。通过使用己二胺，优点地产生二聚体结构，二肽通过它们的羧基团连接到己二胺上。所述化合物在细胞模型中显示出神经保护和诱导分化活性，并在浓度范围为10^(-9)到10^(-5)M时增加了磷酸化酪氨酸激酶A和热休克蛋白Hsp32和Hsp70的量。它们还在动物模型中显示出神经保护、抗帕金森病、抗中风、抗缺血、抗抑郁和抗遗忘活性，并在阿尔茨海默病的实验模型中活跃。所述化合物的这些体内效应在腹腔内给药时的剂量范围为0.01至10毫克/千克。
• Multigram-Scale Synthesis of Short Peptides via a Simplified Repetitive Solution-Phase Procedure
  作者：Célia Meneses、Sarah L. Nicoll、Laurent Trembleau

  DOI：10.1021/jo902116p

  日期：2010.2.5

  A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluorophenyl active esters in a THF/water solvent mixture. Due to their poor solubility, peptide acid intermediates are easily isolated in high purity by acidification under controlled

  描述了肽的快速重复溶液相合成。该方法涉及在THF /水溶剂混合物中，将氨基酸和肽酸（而不是通常的氨基酯和肽酯）偶联到稍微过量的五氟苯基活性酯上。由于它们的溶解性差，因此容易通过在受控条件下酸化并通过选择性萃取除去过量的活性酯，以高纯度分离出肽酸中间体。与现代的重复溶液阶段肽合成程序相反，我们的方法不需要费时的中和反应，并且显着减少了获得肽中间体所需的操作单元数。快速合成疏水性和亲水性短肽证明了该方法的有效性，
• Synthesis of conjugates between oxazolidinone antibiotics and a pyochelin analogue
  作者：Aurélie Paulen、Françoise. Hoegy、Béatrice. Roche、Isabelle J. Schalk、Gaëtan L.A. Mislin

  DOI：10.1016/j.bmcl.2017.09.039

  日期：2017.11

  for severe infections, and it is naturally resistant to many clinically approved antibiotic families. Oxazolidinone antibiotics are active against many Gram-positive bacteria, but are inactive against P. aeruginosa. Increasing the uptake of oxazolidinones through the bacterial envelope could lead to an increased antibiotic effect. Pyochelin is a siderophore of P. aeruginosa which delivers external iron

  铜绿假单胞菌是引起严重感染的革兰氏阴性致病菌，对许多临床批准的抗生素家族具有天然抗性。恶唑烷酮抗生素对许多革兰氏阳性细菌有活性，但对铜绿假单胞菌则无活性。通过细菌包膜增加对恶唑烷酮的吸收可导致增强的抗生素作用。pychelin是铜绿假单胞菌的铁载体它可以将外部铁输送到细菌细胞质中，并且是开发特洛伊木马恶唑烷酮共轭物的潜在载体。使用胺官能化的秋水仙素和末端羧酸盐官能化的恶唑烷酮之间的意外区域选择性肽偶联，合成了新型的pyochelin-恶唑烷酮共轭物。