(S)-N-Fmoc-乙烯基甘氨酸 | 1025434-04-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (S)-N-Fmoc-乙烯基甘氨酸
• 中文别名: (S)-2-((((9H-芴-9-基)甲氧基)羰基)氨基)丁-3-烯酸
• 英文名称: (S)-N-(Fmoc)vinylglycine
• 英文别名: Fmoc-L-Vinylglycine；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)but-3-enoic acid
• CAS: 1025434-04-1
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: WKYFUFWCJIKRCS-KRWDZBQOSA-N

物化性质

• 沸点：
  559.9±45.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  (S)-N-Fmoc-乙烯基甘氨酸 在 Ru-containing catalyst 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 tert-butyl 2-[(3S,4Z)-8-bromo-3-(9H-fluoren-9-ylmethoxycarbonylamino)-2-oxo-3,6-dihydro-1-benzazocin-1-yl]acetate
  参考文献：
  名称：

  A modular, general and enantiospecific strategy for the synthesis of CVS 1778 analogs: inhibitors of factor Xa

  摘要：

  A modular synthetic route has been developed for the synthesis of a series of complex benzalactams which are potent inhibitors of factor Xa. The route produces fused benzalactams of varying ring size via a key-step ring-closing metathesis reaction. The route also facilitates the synthesis of discrete enantiomers using readily available commercial building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01924-x
• 作为产物：
  描述：

  Fmoc-L-Met-OMe 在 盐酸 、 sodium periodate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 xylene 为溶剂， 反应 140.0h， 生成 (S)-N-Fmoc-乙烯基甘氨酸
  参考文献：
  名称：

  A modular, general and enantiospecific strategy for the synthesis of CVS 1778 analogs: inhibitors of factor Xa

  摘要：

  A modular synthetic route has been developed for the synthesis of a series of complex benzalactams which are potent inhibitors of factor Xa. The route produces fused benzalactams of varying ring size via a key-step ring-closing metathesis reaction. The route also facilitates the synthesis of discrete enantiomers using readily available commercial building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01924-x

文献信息

• Peptidomimetic Synthesis by Way of Diastereoselective Iodoacetoxylation and Transannular Amidation of 7–9-Membered Lactams
  作者：N. D. Prasad Atmuri、David J. Reilley、William D. Lubell

  DOI：10.1021/acs.orglett.7b02275

  日期：2017.10.6

  Azacyclo- and azabicycloalkanone peptidomimetics were synthesized regio- and diastereoselectively by iodoacetoxylation and transannular amidation reactions on unsaturated lactam precursors contingent on ring size, olefin position, solvent, and hypervalent iodine(III) reagent. 4-Iodopyrrolizidinone 1, 7-iodoindolizidinone 2, and 4-iodo-5-acetoxylactams (e.g., 6 and 7) were made stereospecifically from

  通过碘乙酰氧基化和在不饱和内酰胺前体上进行环戊酰胺化反应，根据环的大小，烯烃位置，溶剂和高价碘（III）试剂，区域和非对映选择性地合成氮杂环和氮杂双环烷酮的拟肽。4- Iodopyrrolizidinone 1，7- iodoindolizidinone 2，和4-碘-5- acetoxylactams（例如，6和7）的立体有择性从7-9元烯烃制成16，碘和高价碘（III）在乙腈或甲苯中，分别。X射线晶体学显示出模仿天然肽转向侧链和主链构象的潜力。
• Insight into Transannular Cyclization Reactions To Synthesize Azabicyclo[<i>X</i>.<i>Y</i>.<i>Z</i>]alkanone Amino Acid Derivatives from 8-, 9-, and 10-Membered Macrocyclic Dipeptide Lactams
  作者：N. D. Prasad Atmuri、William D. Lubell

  DOI：10.1021/acs.joc.5b00237

  日期：2015.5.15

  An efficient method for synthesizing different functionalized azabicyclo[X.Y.0]alkanone amino acid derivatives has been developed employing electrophilic transannular cyclizations of 8-, 9-, and 10-membered unsaturated macrocycles to form 5,5-, 6,5-, 7,5-, and 6,6-fused bicylic amino acids, respectively. Macrocycles were obtained by a sequence featuring peptide coupling of vinyl-, allyl-, homoallyl-

  一种合成不同功能化氮杂双环[ X的有效方法。ÿ.0]烷酮氨基酸衍生物是利用8、9和10元不饱和大环的亲电跨环环化反应形成5、5、6、5、7、5和6，6稠合的双环氨基酸。通过以乙烯基-，烯丙基-，高烯丙基-和高同烯丙基甘氨酸结构单元的肽偶联为特征，然后闭环易位的序列获得大环。对8元，9元和10元大环内酰胺起始原料以及某些双环氨基酸产物的X射线晶体学分析提供了对它们的构象偏爱以及非对映选择性形成特定氮杂双环烷酮氨基酸的机理的见解。环戊内酰胺化反应的方式。
• [EN] TRIAZOLE-CROSSLINKED AND THIOETHER-CROSSLINKED PEPTIDOMIMETIC MACROCYCLES<br/>[FR] MACROCYCLES PEPTIDOMIMÉTIQUES RÉTICULÉS PAR TRIAZOLE ET PAR THIOÉTHER
  申请人：AILERON THERAPEUTICS INC

  公开号：WO2013123267A1

  公开（公告）日：2013-08-22

  Provided herein are peptidomimetic macrocycles and methods of using such macrocycles for the treatment of disease.

  本文提供了肽类模拟大环和使用这种大环治疗疾病的方法。
• Synthesis of conformationally constrained γ-d-glutamyl-meso-diaminopimelic acid derivatives as ligands of nucleotide-binding oligomerization domain protein 1 (Nod1)
  作者：Žiga Jakopin、Martina Gobec、Jaka Kodela、Toni Hazdovac、Irena Mlinarič-Raščan、Marija Sollner Dolenc

  DOI：10.1016/j.ejmech.2013.08.022

  日期：2013.11

  Nod1, an important member of the pattern recognition receptor family, remains a virtually unexploited target. Harnessing its innate immune stimulatory properties still remains an unfulfilled goal of medicinal chemistry. Nucleotide-binding oligomerization domain protein 1 (Nod1) agonists have been shown to boost the inflammatory responses against pathogenic microbes and could thus constitute a new class of broad spectrum antimicrobial agents. To gain additional insight into the structure/activity relationships of Nod1 agonistic compounds, a series of novel, conformationally constrained gamma-D-glutamyl-meso-diaminopimelic acid (iE-DAP) analogs have been designed and synthesized. Ramos-Blue cells expressing Nod1 were used to screen and validate our compounds for their Nod1-agonist activity. Their immunomodulatory properties were subsequently determined in vitro, by evaluating their capacity to induce proinflammatory cytokine and chemokine production from human peripheral blood mononuclear cells (PBMC), by themselves and in synergy with lipopolysaccharide (LPS), a Toll-like receptor 4 (TLR4) ligand. The synthesized iE-DAP analogs were shown to possess immuno-enhancing properties as a result of their potent and specific Nod1-agonistic effect. The activity of the compound exhibiting the greatest capacity to induce pro-inflammatory cytokine release from PBMC surpassed that of lauroyl-gamma-D-glutamyl-mesodiaminopimelic acid (C12-iE-DAP). (C) 2013 Elsevier Masson SAS. All rights reserved.
• [EN] METHOD FOR DETECTING AN ANALYTE OF INTEREST IN A SAMPLE<br/>[FR] PROCÉDÉ DE DÉTECTION D'UN ANALYTE D'INTÉRÊT DANS UN ÉCHANTILLON
  申请人：[en]F. HOFFMANN-LA ROCHE AG

  公开号：WO2022136234A1

  公开（公告）日：2022-06-30

  The present invention relates to a method for determining at least one analyte of interest. The present invention further relates to a kit, a complex, a method to synthesize a complex and the use thereof for detecting the analyte of interest in the sample.