甲基N6-[(苄氧基)羰基]-D-赖氨酸酯盐酸盐(1:1) | 1158-35-6

• 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
• 中文名称: 甲基N6-[(苄氧基)羰基]-D-赖氨酸酯盐酸盐(1:1)
• 中文别名: N'-苄氧羰基-D-赖氨酸甲酯盐酸盐；H-D-赖氨酸(Z)-甲酯盐酸盐
• 英文名称: N^ε-benzyloxycarbonyl-D-lysine methyl ester hydrochloride
• 英文别名: (R)-methyl 2-amino-6-(((benzyloxy)carbonyl)amino)hexanoate hydrochloride；H-D-Lys(Z)-OMe HCl；methyl (2R)-2-amino-6-(phenylmethoxycarbonylamino)hexanoate;hydrochloride
• CAS: 1158-35-6
• 化学式: C₁₅H₂₂N₂O₄*ClH
• 分子量: 330.812
• InChiKey: QPNJISLOYQGQTI-BTQNPOSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90.6
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气氛

反应信息

• 作为反应物：
  描述：

  甲基N6-[(苄氧基)羰基]-D-赖氨酸酯盐酸盐(1:1) 在 10 percent Pd/C N-甲基吗啉 、 lithium hydroxide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-[4-(((3,5-dimethylanilino)carbonyl)methyl)phenoxy]cyclopentanecarbonyl-D-lysine
  参考文献：
  名称：

  Synthesis and X-ray Studies of Chiral Allosteric Modifiers of Hemoglobin

  摘要：

  This study was designed to investigate the effect of chirality on the allosteric activity of a series of Hb allosteric modifiers. The chiral analogues were based on the lead compound (4), JP7, {1-[4-(((3,5-dimethylanilino)carbonyl)methyl)phenoxy]cyclopentanecarboxylic acid} with different D- and L-amino acids conjugated to the JP7 acid moiety. The D-isomers were the most potent in vitro effectors in Hb solutions as well as with whole blood. In general, this study demonstrated that the chirality of extended amino acid side chains in JP7 conjugates plays an important role in observed degree of allosteric activity. The binding site interactions for four analogues were determined by single crystallographic diffraction studies. Conclusions show that the chiral configuration of some of the D-isomers enable the effectors to bind with a greater number of interactions with the protein residues. D- and L-isomers with equivalent or near equivalent allosteric activity did not show any significant differences or interactions between their amino acid side chains and the protein. The most potent effectors, in vitro, were compounds 15 and 19, D-isomers of leucine and phenylalanine, respectively. Compounds 21, 22, 30, and 32 were more potent in vitro in Hb solutions than JP7.

  DOI：

  10.1021/jm010358l
• 作为产物：
  描述：

  在 盐酸 作用下， 反应 30.0h， 生成 甲基N6-[(苄氧基)羰基]-D-赖氨酸酯盐酸盐(1:1)
  参考文献：
  名称：

  Wang, Qiang; Shi, Qiao; Huang, Lu, Letters in drug design and discovery, 2016, vol. 13, # 1, p. 98 - 106

  摘要：

  DOI：

文献信息

• Synthese von cyclischen Pentapeptidanalogen des Thymopoietins. – Cyclisierungen mit Carbodiimid und 4-(Dimethylamino)pyridin
  作者：Horst Kessler、Bernhard Kutscher

  DOI：10.1002/jlac.198619860507

  日期：1986.5.13

  Die Synthesen von zehn cyclischen Pentapeptiden mit Thymopoietin-analogen Sequenzen werden beschrieben. Die linearen Vorstufen der Cyclen wurden nach klassischen Methoden der Peptidchemie synthetisiert. Die Cyclisierungen erfolgten mit der neu entwickelten Carbodiimid/DMAP-Methode, deren Vorteile bezüglich Ausbeute und Reinheit gegenüber der Azidmethode nach Medzhiradsky aufgezeigt werden. Die starke

  描述了十种具有胸腺生成素类似序列的环状五肽的合成。根据经典的肽化学方法合成了循环的线性前体。使用新开发的碳二亚胺/ DMAP方法进行环化反应，与Medzhiradsky叠氮化物方法相比，其在产率和纯度方面的优势得以体现。如果线性前体不包含任何C端或N端D-氨基酸，则强活化导致C端外消旋或反转。
• Studies of Peptide Antibiotics. I. Dipeptide Anhydrides as Models of Cyclic Peptide Antibiotics
  作者：Nobuo Izumiya、Tetsuo Kato、Yoshimasa Fujita、Motonori Ohno、Michio Kondo

  DOI：10.1246/bcsj.37.1809

  日期：1964.12

  The D-D, L-L, D-L and L-D stereomers of both valyllysine anhydride and phenylalanyllysine anhydride, and the D-L and L-L stereomers of both valylornithine anhydride and phenylalanylornithine anhydride, have been synthesized in order to compare them with the cyclic peptide antibiotics, with which they possess several structural features in common. Synthesis has been achiveved by the dicyclohexylcarbodiimide-induced

  合成了缬氨酰酐和苯丙赖氨酸酐的 DD、LL、DL 和 LD 立体异构体，以及缬氨酰鸟氨酸酐和苯丙氨酸酐酐的 DL 和 LL 立体异构体，以便与环肽类抗生素进行比较。共同的结构特点。合成是通过二环己基碳二亚胺诱导的甲酰基（或叔丁氧羰基）缬氨酸（或苯丙氨酸）与 ω-羧基苯甲氧基赖氨酸（或鸟氨酸）酯的缩合，然后在甲醇中用氯化氢处理所得酰基二肽酯来实现的或乙酸乙酯去除甲酰基或叔丁氧羰基保护基团。如此衍生的二肽酯盐酸盐已在氨的作用下转化为相应的苯甲氧基取代的二肽酸酐，而这些又通过钯催化的氢解转化为所需的未酰化的二肽酸酐盐酸盐。酶解...
• 1,3-dihydroindol-2-one derivatives substituted in the 3-position by a
  申请人：Sanofi

  公开号：US05594023A1

  公开（公告）日：1997-01-14

  The present invention relates to compounds of formula (I) and salts thereof, where appropriate: ##STR1## These compounds have an affinity for the vasopressin and/or ocytocin receptors.

  本发明涉及式(I)化合物及其盐，如适用：这些化合物具有对加压素和/或催产素受体的亲和力。
• Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins
  作者：Andrea Mascitti、Massimiliano Lupacchini、Ruben Guerra、Ilya Taydakov、Lucia Tonucci、Nicola d’Alessandro、Frederic Lamaty、Jean Martinez、Evelina Colacino

  DOI：10.3762/bjoc.13.3

  日期：——

  The mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins was investigated in the presence of various poly(ethylene) glycols (PEGs), as safe grinding assisting agents (liquid-assisted grinding, LAG). A comparative study under dry-grinding conditions was also performed. The results showed that the cyclization reaction was influenced by the amount of the PEG grinding agents

  在作为安全研磨助剂（液体辅助研磨，LAG）的各种聚乙二醇（PEG）存在下，研究了高度官能化的3,5-二取代乙内酰脲的机械化学制备。还进行了干磨条件下的比较研究。结果表明，环化反应受PEG研磨剂的量影响。通常，与干研磨程序相比，在PEG存在下观察到更干净的反应曲线。
• A Cyclic Enamine Derived from 1,2-<i>O</i>-Isopropylidene-α-<scp>d</scp>-xylofuranose As a Novel Carbohydrate Intermediate To Achieve Skeletal Diversity
  作者：Alessandra Cordeiro、Ernesto Quesada、María-Cruz Bonache、Sonsoles Velázquez、María-José Camarasa、Ana San-Félix

  DOI：10.1021/jo0609531

  日期：2006.9.1

  easy purifications) into fused cyclic sugar derivatives with rather unusual molecular skeletons in a completely regio- and stereoselective manner. The characteristics of the sugar derivative 8 established here, high reactivity, synthetic accessibility, and the potential for conversion into a vast collection of products by the action of different nucleophiles, indicate that it will prove to be a useful

  商业上可获得的碳水化合物1,2 - O-异亚丙基-α- d-木呋喃糖被有效地转化为高附加值的合成支架8。该转化需要在基本条件下合成5- O-甲苯磺酰基衍生物7及其随后的分子内环化反应，以得到环状烯胺8。反应8与ø - ，Ñ - ，小号-和C-亲核试剂和氨基酸使其能够以完全的区域选择性和立体选择性方式高效转化（一步，高收率和易于纯化），转变为具有异常分子骨架的稠合环状糖衍生物。此处建立的糖衍生物8的特性，高反应活性，合成可及性以及通过不同亲核试剂的作用转化为大量产品的潜力，表明它将被证明是实现骨骼多样性的有用手性中间体。由8生成的多环糖衍生物的结构受限和稠密的功能化，使得这些化合物有望成为候选物，用作生产新类似物和药物的起始剂。