2,5-二氧代-1-吡咯烷基O-苄基-N-[(苄氧基)羰基]-L-丝氨酸酯 | 98647-23-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二氧代-1-吡咯烷基O-苄基-N-[(苄氧基)羰基]-L-丝氨酸酯
• 英文名称: Cbz-Ser(OBn)-OSu
• 英文别名: O-benzyl-N^α-benzyloxycarbonylserine succinimidyl ester；N-carbobenzoxy-O-benzyl-L-serine N-succinimidyl ester；ester N-hydroxysuccinimyle de la N-benzyloxycarbonyl-O-benzyl-L-serine；Z-Ser(bzl)-osu；(2,5-dioxopyrrolidin-1-yl) (2S)-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 98647-23-5
• 化学式: C₂₂H₂₂N₂O₇
• 分子量: 426.426
• InChiKey: FENPPJIIQWZISH-SFHVURJKSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-二氧代-1-吡咯烷基O-苄基-N-[(苄氧基)羰基]-L-丝氨酸酯 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (S)-N-benzyloxycarbonyl O-benzyl serinamide
  参考文献：
  名称：

  A stereocontrolled synthesis of a new class of 3,4,5,6-tetrahydropyrimidine-based chiral amino acids

  摘要：

  The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6-tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine. (S)- and (R serine, (S)- and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00177-5
• 作为产物：
  描述：

  O-苄基-L-丝氨酸 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 2.0h， 生成 2,5-二氧代-1-吡咯烷基O-苄基-N-[(苄氧基)羰基]-L-丝氨酸酯
  参考文献：
  名称：

  A stereocontrolled synthesis of a new class of 3,4,5,6-tetrahydropyrimidine-based chiral amino acids

  摘要：

  The stereocontrolled synthesis of seven 2-substituted-4-carboxy-3,4,5,6-tetrahydropyrimidines bearing either one chiral center at C-4 or two chiral centers at C-4 and C-8 was performed by condensation of (S)- or (R)-2, 4-diaminobutyric acid (Daba) with iminoethers derived from glycine. (S)- and (R serine, (S)- and (R)-tyrosine. Under the conditions reported, epimerization was always completely prevented at the C-4 center, whereas at the C-8 center, it was completely avoided in the case of tyrosine derivatives and considerably diminished for the serine derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00177-5

文献信息

• Synthesis and Platelet-Activating Factor (PAF)-Antagonistic Activities of Trisubstituted Piperazine Derivatives.
  作者：Hideto FUKUSHI、Hiroshi MABUCHI、Zen-ichi TERASHITA、Kohei NISHIKAWA、Hirosada SUGIHARA

  DOI：10.1248/cpb.42.551

  日期：——

  2- or 3-Substituted 1-(2, 3-dimethoxy-6, 7-dihydro-5H-benzocyclohepten-8-ylcarbonyl)-4-(3, 4, 5-trimethoxybenzoyl)- and 4-(3, 4, 5-trimethoxybenzyl)piperazines (2a-s, 3a, b) were prepared and evaluated for antagonistic activities against platelet-activating factor (PAF)-induced platelet aggregation and blood pressure reduction. The 2-methoxymethyl derivative (2f) showed the most potent activities in this series. The enantiomers (R)-(+)-2f and (S)-(-)-2f were synthesized from carbobenzoxy-O-benzyl-L- and D-serine in several steps. In the binding experiment, (S)-(-)-2f showed thirty times greater affinity than the R isomer for the PAF receptor.

  2-或3-取代的1-(2,3-二甲氧基-6,7-二氢-5H-苯并环庚烯-8-基羰基)-4-(3,4,5-三甲氧基苯甲酰基)和4-(3,4,5-三甲氧基苄基)哌嗪（2a-s，3a，b）被制备并评估了它们对血小板活化因子（PAF）诱导的血小板聚集和血压降低的拮抗活性。其中，2-甲氧甲基衍生物（2f）显示出系列中最强的活性。从苄氧羰基-O-苄基-L-和D-丝氨酸经过几个步骤合成了其对映体（R）-(+)-2f和（S）-(-)-2f。在结合实验中，（S）-(-)-2f对PAF受体的亲和力是R异构体的三十倍。
• Study on the Structure Activity Relationships of NPTX-594, a Spider Toxin Belonging to the Type-B Acylpolyamine Structure
  作者：Tateaki Wakamiya、Tomohiko Kinoshita、Yoshihide Hattori、Yoshihiro Yamaguchi、Hideo Naoki、Gerardo Corzo、Terumi Nakajima

  DOI：10.1246/bcsj.77.331

  日期：2004.2

  In order to elucidate the structure activity relationships of the spider toxin termed NPTX-594, eleven toxin analogs were designed and synthesized, and their paralytic activities against cricket we...

  为了阐明被称为 NPTX-594 的蜘蛛毒素的构效关系，设计并合成了 11 种毒素类似物，以及它们对蟋蟀的麻痹活性...
• Antigenes de groupe sanguin
  作者：B. Ferrari、A.A. Pavia

  DOI：10.1016/s0040-4020(01)96557-3

  日期：1985.1

  and proceeding toward the N-terminus, using amino acids or suitably protected and activated O-glycosyl-amino acids. Carbohydrate residues were introduced into the sequence as 2-azido-2-deoxy-α-D-galactopyranosyl-l-serine and l-thréonine derivatives obtained from the reducing sugar and amino acid by the trifluoromethanesulfonic anhydride procedure. Reduction of the azido functions followed by acetylation

  该报告描述了三糖基化五肽H 2 N-Leu-Se * r-Th * r-Th * r-Gl * u-OH和H 2 N-Ser-Se * r-Th * r-Th *的首次合成r-Glu-OH，其中*表示2-乙酰氨基-2-脱氧α-D-吡喃半乳糖基残基。这些化合物分别构成人糖蛋白A N和A Mc的抗原性氨基末端部分。通过在溶液中从C端开始向N端逐步肽偶联策略获得上述化合物-末端，使用氨基酸或适当保护和活化的O-糖基-氨基酸。通过三氟甲磺酸酐方法，将碳水化合物残基作为2-叠氮基-2-脱氧-α-D-吡喃半乳糖基-1-丝氨酸和1-苏氨酸衍生物引入序列中。还原叠氮基官能团，随后乙酰化和催化氢解，得到上述抗原性T N糖基化五肽。
• Direct PCR amplification of various modified DNAs having amino acids: Convenient preparation of DNA libraries with high-potential activities for in vitro selection
  作者：Masayasu Kuwahara、Kazuo Hanawa、Kazuomi Ohsawa、Rina Kitagata、Hiroaki Ozaki、Hiroaki Sawai

  DOI：10.1016/j.bmc.2005.11.030

  日期：2006.4

  We synthesized modified 2'-deoxyuridine triphosphates bearing amino acids at the C5 position and investigated their substrate properties for KOD Dash DNA polymerase during polymerase chain reaction (PCR). PCR using C5-modified dUTP having an amino acyl group (arginyl, histidyl, lysyl, phenylalanyl, tryptophanyl, leucyl, prolyl, glutaminyl, seryl, O-benzyl seryl or threonyl group) gave the corresponding full-length PCR products in good yield. Although dUTP analogues bearing aspartyl, glutamyl or cysteinyl were found to be poor substrates for PCR catalyzed by KOD Dash DNA polymerase, optimization of the reaction conditions resulted in substantial generation of full-length product. In the case of reaction using dUTP analogue having a cysteinyl group, addition of a reducing agent improved the reaction yield. Thus, PCRs using KOD Dash DNA polymerase together with amino acyl dUTP provide convenient and efficient preparation of various modified DNA libraries with potential protein-like activities. (c) 2005 Elsevier Ltd. All rights reserved.
• Possible role of the carbohydrate residues on the structure of the n-terminus of glycophorin AM
  作者：Killian Dill、R.Douglas Carter、Jean M. Lacombe、André A. Pavia

  DOI：10.1016/s0008-6215(00)90301-x

  日期：1986.9

  Natural-abundance 13C nuclear magnetic resonance (13C-n.m.r.) was used to study the effect of monoglycosylation on the structure and dynamics of a pentapeptide related to the N-terminus of glycophorin AM. The results of this study indicate that a single point of glycosylation, on the pentapeptide, can significantly affect its structure. Moreover, glycosylation of this pentapeptide also affects its dynamic motion in solution. This study further defines the role that the carbohydrate residue plays in determining the structure about the N-terminus of glycophorin AM.