N-[芴甲氧羰基]-D-谷氨酸烯丙基酯 | 204251-86-5

• 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
• 中文名称: N-[芴甲氧羰基]-D-谷氨酸烯丙基酯
• 中文别名: FMOC-D-谷氨酸-1-烯丙酯
• 英文名称: N-α-Fmoc-D-glutamic acid-α-allyl ester
• 英文别名: Fmoc-Dglu(OAllyl)OH；D-Fmoc-Glu-OAll；Fmoc-D-Glu-OAllyl；Fmoc-D-Glu-1-allyl ester；(R)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid；Fmoc-α-allyl-D-glutamate；Fmoc-Glu-OAll；(4R)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
• CAS: 204251-86-5
• 化学式: C₂₃H₂₃NO₆
• 分子量: 409.439
• InChiKey: ORKKMGRINLTBPC-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  N-[芴甲氧羰基]-D-谷氨酸烯丙基酯 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成
  参考文献：
  名称：

  Structure−Activity Relationships in Nucleotide Oligomerization Domain 1 (Nod1) Agonistic γ-Glutamyldiaminopimelic Acid Derivatives

  摘要：

  N-Acyl-gamma-glutamyldiaminopimelic acid is a prototype ligand for Nod1. We report a detailed SAR of C-12-gamma-D-Glu-DAP. Analogues with glutaric or gamma-aminobutyric acid replacing the glutamic acid show greatly attenuated Nod1-agonistic activity. Substitution of the meso-diaminopimelic (DAP) acid component with monoaminopirnelic acid, L- or D-lysine, or cadaverine also results in reduced activity. The free amine on DAP is crucial. However, the N-acyl group on the D-glutamyl residue can be substituted with N-alkyl groups with full preservation of activity. The free carboxylates on the DAP and Glu components can also be esterified, resulting in more lipophilic but active analogues. Transcriptomal profiling showed a dominant up-regulation of IL-19, IL-20, IL-22, and IL-24, which may explain the pronounced Th2-polarizing activity of these compounds and also implicate cell signaling mediated by TREM-1. These results may explain the hitherto unknown mechanism of synergy between Nod1 and TLR agonists and are likely to be useful in designing vaccine adjuvants.

  DOI：

  10.1021/jm101535e
• 作为产物：
  描述：

  BOC-D-谷氨酸5-叔丁酯 在 4-二甲氨基吡啶 、 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 N-[芴甲氧羰基]-D-谷氨酸烯丙基酯
  参考文献：
  名称：

  Structure−Activity Relationships in Nucleotide Oligomerization Domain 1 (Nod1) Agonistic γ-Glutamyldiaminopimelic Acid Derivatives

  摘要：

  N-Acyl-gamma-glutamyldiaminopimelic acid is a prototype ligand for Nod1. We report a detailed SAR of C-12-gamma-D-Glu-DAP. Analogues with glutaric or gamma-aminobutyric acid replacing the glutamic acid show greatly attenuated Nod1-agonistic activity. Substitution of the meso-diaminopimelic (DAP) acid component with monoaminopirnelic acid, L- or D-lysine, or cadaverine also results in reduced activity. The free amine on DAP is crucial. However, the N-acyl group on the D-glutamyl residue can be substituted with N-alkyl groups with full preservation of activity. The free carboxylates on the DAP and Glu components can also be esterified, resulting in more lipophilic but active analogues. Transcriptomal profiling showed a dominant up-regulation of IL-19, IL-20, IL-22, and IL-24, which may explain the pronounced Th2-polarizing activity of these compounds and also implicate cell signaling mediated by TREM-1. These results may explain the hitherto unknown mechanism of synergy between Nod1 and TLR agonists and are likely to be useful in designing vaccine adjuvants.

  DOI：

  10.1021/jm101535e

文献信息

• [EN] BETA-HAIRPIN PEPTIDOMIMETICS<br/>[FR] PEPTIDOMIMÉTIQUES EN ÉPINGLE À CHEVEUX BÊTA
  申请人：POLYPHOR AG

  公开号：WO2016150576A1

  公开（公告）日：2016-09-29

  Beta-hairpin peptidomimetics of the general formula (I), and pharmaceutically acceptable salts thereof, with P, T, Q., and optionally L being elements as defined in the description and the claims, have Gram-negative antimicrobial activity to e.g. inhibit the growth or to kill microorganisms such as Klebsiellapneumoniae and/or Acinetobacter baumannii and/or Escherichia coli and/or Pseudomonas aeruginosa. They ca n be used as medicaments to treat or prevent infections or as disinfectants for foodstuffs, cosmetics, medicaments or other nutrient-containing materials. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  Beta-发夹仿生肽的一般公式（I），及其药学上可接受的盐，其中P、T、Q.，以及可选的L作为描述和权利要求中定义的元素，具有抗革兰氏阴性微生物活性，例如抑制生长或杀灭肺炎克雷伯菌、包括鲍曼不动杆菌、大肠杆菌和铜绿假单胞菌等微生物。它们可用作药物治疗或预防感染，或用作食品、化妆品、药物或其他含营养物质的材料的消毒剂。这些仿生肽可以通过基于混合固相和溶液相合成策略的过程制造。
• Generation of a cell-permeable cycloheptapeptidyl inhibitor against the peptidyl–prolyl isomerase Pin1
  作者：Walaa Bedewy、Hui Liao、Nageh A. Abou-Taleb、Sherif F. Hammad、Tamer Nasr、Dehua Pei

  DOI：10.1039/c7ob00430c

  日期：——

  Integration of Pin1-binding and cell-penetrating sequences results in a cell-permeable, biologically active cycloheptapeptide inhibitor against Pin1.

  将Pin1结合和穿透细胞序列集成在一起，得到了一种针对Pin1的可穿透细胞、生物活性的环庚肽抑制剂。
• Cyclopropylindole derivatives
  申请人：Thurston David Edwin

  公开号：US06909006B1

  公开（公告）日：2005-06-21

  Compounds of formula (III) or (V), wherein is a solid support; L is a linking group or a single bond; T is a combinatorial unit; n is a positive integer, where if n is greater than 1, each T may be different: X is an electrophilic leaving group; Y is selected from NH-Prot, O-Prot, S-Prot, NO 2 , —NHOH. N 3 , NHR, NRR, N═NR, N(O)RR, NHSO 2 R, N═N═PhR, SR or SSR, where Prot represents a protecting group; A and B collectively represent a fused benzene or pyrrole ring (in either orientation), which is optionally substituted by up to respectively 4 or 2 groups independently selected from R, OH, OR, halo, nitro, amino, Me 3 Sn, CO 2 H, CO 2 R, R 1 is a nitrogen protecting group, where if Y includes a protecting group, these protecting groups are orthogonal and R 2 and R 7 are independently selected from H, R, OH, OR, halo, nitro, amino, Me 3 Sn, and other related compounds and collections of compounds.

  式（III）或（V）的化合物中，其中是固体支撑；L是连接基团或单键；T是组合单元；n是正整数，如果n大于1，则每个T可能不同：X是亲电离开基团；Y从NH-Prot、O-Prot、S-Prot、NO2、—NHOH、N3、NHR、NRR、N═NR、N（O）RR、NHSO2R、N═N═PhR、SR或SSR中选择，其中Prot代表保护基团；A和B共同代表一个融合的苯或吡咯环（在任何方向），可选地由最多分别从R、OH、OR、卤、硝基、氨基、Me3Sn、CO2H、CO2R中独立选择的4个或2个基团取代，R1是氮保护基团，如果Y包括保护基团，则这些保护基团是正交的，R2和R7分别独立选择自H、R、OH、OR、卤、硝基、氨基、Me3Sn和其他相关化合物和化合物集合。
• Bead diffusion assay for discovering antimicrobial cyclic peptides
  作者：Viviana S. Fluxà、Noélie Maillard、Malcolm G. P. Page、Jean-Louis Reymond

  DOI：10.1039/c0cc04670a

  日期：——

  A combinatorial library of 15,536 cyclic decapeptide analogues of tyrocidine A and gramicidin S was prepared on photocleavable TentaGel beads. The beads were photolyzed without solvent, and spread onto an agar plate inoculated with bacterial lawn. Clear zones were formed around beads carrying antimicrobially active peptides such as E18 c(kVOrnLfThiYOrnLq), which inhibited growth of B. subtilis and

  在光可裂解的TentaGel珠上制备了酪氨酸A和短杆菌肽S的15,536个环状十肽类似物的组合文库。将珠子在无溶剂的情况下光解，并铺在接种有细菌性草坪的琼脂平板上。在带有抗微生物活性肽（例如E18 c（kVOrnLfThiYOrnLq））的珠子周围形成了清晰的区域，该肽可抑制枯草芽孢杆菌和某些MRSA菌株的生长。
• CYCLIC PEPTIDE CXCR4 ANTAGONISTS
  申请人：Kohn Wayne David

  公开号：US20080300177A1

  公开（公告）日：2008-12-04

  Provided are lactam-cyclized peptide CXCR4 antagonists useful in the treatment of cancers, rheumatoid arthritis, pulmonary fibrosis, and HIV infection.

  提供了在治疗癌症、类风湿关节炎、肺纤维化和HIV感染中有用的内酰胺环化肽CXCR4拮抗剂。