CAS: 84000-07-7; Fmoc-N-Me-Ala-Oh

该化合物是氨酸L-alaine的衍生物,用氟烯烃-碳酸(Fmoc)来修改保护该物质.该化合物的特点是在peptide合成中使用该物质,特别是在固相peptide合成(SPPS)中,该物质组是氨酸氨酸氨基组的一个临时保护组.Fmoc组在基本条件下因其稳定性而著称,可以在温酸条件下被清除,允许在peptide链中依次添加氨酸.亚硝酸侧链氮原子上的甲基组的存在会增强分子的胃特性,影响其再活性和溶解性.此外,氟化基化合物组有助于复合的氢恐惧性特性,这可以影响氨基氨基化合物在硫化物合成场的总体特性.

英文名称Fmoc-N-Me-Ala-Oh
中文名称Fmoc-N-甲基-L-丙氨酸
IUPAC名称N-(((9H-fluoren-9-yl)methoxy)carbonyl)-N-methyl-L-alanine
其它别名FM°C-N-Me-Ala-OH; N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-alpha-methyl-L-alanine
CAS编号84000-07-7
MFCD编号:MFCD00153384
EINECS号:197-513-6
分子式:C19H19NO4
分子量:325.36
产品CID: 1828354
产品分类生物化工 → 氨基酸及其衍生物 → 丙氨酸类衍生物

相似结构搜索
InChIKey: JOFHWKQIQLPZTC-LBPRGKRZSA-N
InChI=1S/C19H19NO4/c1-12(18(21)22)20(2)19(23)24-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17H,11H2,1-2H3,(H,21,22)/t12-/m0/s1…
计算化学: 氢键受体数4.0氢键供体数1.0可旋转键数5.0

物理性质

熔点~150 °C
沸点514.9±29.0 °C at 760 mmHg
闪点265.2±24.3 °C
密度1.3±0.1 g/cm3
PH:-18.5 º (c=1,DMF)
pKa:3.92±0.10(预测)
PSA:66.84
LogP:4.03
旋光度-18.5º(C=1,DMF)
折射率1.604
蒸汽压0.0±1.4 mmHg at 25°C
溶解性Soluble In Water Or 1% Acetic Acid
敏感性按规定使用和贮存的不会分解，避氧化物
外观形态白色至几乎白色固体
储存条件2-8°C
产品应用该化合物用于该化合物用于浸泡物合成.

MSDS等安全信息

危险类别特定目标器官毒性 - 单次接触类别3
皮肤腐蚀/刺激类别2
严重眼刺激类别2A
警示词Warning
危险描述H335 |可能引起呼吸道刺激.
H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
防范说明P261-P305+P351+P338-
危险等级IRRITANT
UN编号NONH for all modes of transport
危险品标志Xi
安全声明22-24/25
WGK Germany3

欧盟法规

C&L通报

上下游产品

合成工艺路线路线简述

83999-95-5 = 84000-07-7
反应条件:1.1 Reagents: Trifluoroacetic Acid,Triethylsilane Solvents: Chloroform
标题:Structure Activity Relationship Study Of Callipeltin B For The Cytotoxic Activity
作者:Kikuchi,Mari; Et Al
参考文献:Peptide Science 日期:2013 卷标:49 页码:145-148]

1220527-64-9 = 84000-07-7
反应条件:1.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane,Toluene; 1 H,Rt
标题:A Preparation Of N-Fmoc-N-Methyl-α-Amino Acids And N-Nosyl-N-Methyl-α-Amino Acids
作者:Di Gioia,Maria Luisa; Et Al
参考文献:Amino Acids 日期:2010 卷标:38(1) 页码:133-143]

35661-39-3 = 84000-07-7
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; 30 Min,Reflux; Cooled1.2 Reagents: Trifluoroacetic Acid,Triethylsilane Solvents: Chloroform; 10 H,Rt
标题:Total Synthesis Of Proposed Structure Of Coibamide A,A Highly N- And O-Methylated Cytotoxic Marine Cyclodepsipeptide
作者:He,Wei; Et Al
参考文献:Tetrahedron Letters 日期:2014 卷标:55(44) 页码:6109-6112]

35661-39-3 = 84000-07-7
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid Solvents: Toluene; Rt; 1 H,Reflux1.2 Reagents: Trifluoroacetic Acid,Triethylsilane Solvents: Chloroform; 0 °C; 7 H,Rt
标题:Total Synthesis Of Hytramycin V,An Antibiotic Cyclopeptide
作者:Inaba,Tetsuya; Et Al
参考文献:Bulletin Of The Chemical Society Of Japan 日期:2021 卷标:94(7) 页码:1922-1930]

28920-43-6 + 1208119-53-2 = 84000-07-7
反应条件:1.1 Reagents: Sodium Thiophenolate Solvents: Dimethylformamide; 3 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 21.3 Reagents: Sodium Carbonate Solvents: Water; Ph 9; Rt -> 0 °C1.4 Solvents: 1,4-Dioxane; 3 H,0 °C1.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:An Efficient Preparation Of N-Methyl-α-Amino Acids From N-Nosyl-α-Amino Acid Phenacyl Esters
作者:Leggio,Antonella; Et Al
参考文献:Journal Of Organic Chemistry 日期:2010 卷标:75(5) 页码:1386-1392]

84000-07-7 = 84000-07-7
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 1 H1.2 Reagents: Diisopropylethylamine Solvents: Methanol,Dichloromethane; 20 Min
标题:Total Synthesis Of The Cyclic Depsipeptide Ym-280193,A Platelet Aggregation Inhibitor
作者:Kaur,Harveen; Et Al
参考文献:Organic Letters 日期:2015 卷标:17(3) 页码:492-495]

28920-43-6 + 1220527-52-5 = 84000-07-7
反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Dichloromethane,Water; 1 H,Ph 8,Rt2.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane,Toluene; 1 H,Rt
标题:A Preparation Of N-Fmoc-N-Methyl-α-Amino Acids And N-Nosyl-N-Methyl-α-Amino Acids
作者:Di Gioia,Maria Luisa; Et Al
参考文献:Amino Acids 日期:2010 卷标:38(1) 页码:133-143]

= 84000-07-7
反应条件:1.1 Reagents: Thioglycolic Acid,Sodium Methoxide Solvents: Methanol,Acetonitrile; 40 Min,50 °C2.1 Reagents: Sodium Bicarbonate Solvents: Dichloromethane,Water; 1 H,Ph 8,Rt3.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane,Toluene; 1 H,Rt
标题:A Preparation Of N-Fmoc-N-Methyl-α-Amino Acids And N-Nosyl-N-Methyl-α-Amino Acids
作者:Di Gioia,Maria Luisa; Et Al
参考文献:Amino Acids 日期:2010 卷标:38(1) 页码:133-143]

= 84000-07-7
反应条件:1.1 Solvents: Dichloromethane; Rt; 1.5 H,Rt2.1 Reagents: Thioglycolic Acid,Sodium Methoxide Solvents: Methanol,Acetonitrile; 40 Min,50 °C3.1 Reagents: Sodium Bicarbonate Solvents: Dichloromethane,Water; 1 H,Ph 8,Rt4.1 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane,Toluene; 1 H,Rt
标题:A Preparation Of N-Fmoc-N-Methyl-α-Amino Acids And N-Nosyl-N-Methyl-α-Amino Acids
作者:Di Gioia,Maria Luisa; Et Al
参考文献:Amino Acids 日期:2010 卷标:38(1) 页码:133-143]

83999-95-5 = 84000-07-7
反应条件:1.1 Reagents: Trifluoroacetic Acid,Triethylsilane Solvents: Acetonitrile; 2 H,75 °C
标题:Fluorenylmethoxycarbonyl-N-Methylamino Acids Synthesized In A Flow Tube-In-Tube Reactor With A Liquid-Liquid Semipermeable Membrane
作者:Buba,Annette E.; Et Al
参考文献:European Journal Of Organic Chemistry 日期:2013 卷标:2013(21) 页码:4509-4513]

83999-95-5 = 84000-07-7
反应条件:1.1 Reagents: Trifluoroacetic Acid,Triethylsilane Solvents: Chloroform
标题:Solid Phase Total Synthesis Of Callipeltin E Isolated From Marine Sponge Latrunculia Sp.
作者:Kikuchi,Mari; Et Al
参考文献:Tetrahedron Letters 日期:2011 卷标:52(30) 页码:3872-3875]

28920-43-6 + 59724-75-3 = 84000-07-7
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dimethylformamide,Dichloromethane; 2 H,Rt1.2 Reagents: Methanol,Diisopropylethylamine Solvents: Dichloromethane; 10 Min,Rt1.3 Solvents: Dichloromethane; 4 H,Rt1.4 Reagents: Thiophenol,Potassium Carbonate Solvents: Dimethylformamide; 10 Min,Rt1.5 Solvents: Dimethylformamide; 2 H,Rt1.6 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 2 H,Rt1.7 Reagents: Acetic Acid,2,2,2-Trifluoroethanol Solvents: Dichloromethane; 2 H,Rt
标题:Solid-Phase Synthesis Of N-Nosyl- And N-Fmoc-N-Methyl-α-Amino Acids
作者:Di Gioia,Maria Luisa; Et Al
参考文献:Journal Of Organic Chemistry 日期:2007 卷标:72(10) 页码:3723-3728]

84000-07-7 = 84000-07-7
反应条件:1.1 Reagents: Acetyl Chloride Solvents: Dichloromethane; 4 H,Rt1.2 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 12 H,Rt
标题:Conformation-Based Design And Synthesis Of Apratoxin A Mimetics Modified At The α,β-Unsaturated Thiazoline Moiety
作者:Onda,Yuichi; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2017 卷标:60(15) 页码:6751-6765]

= 84000-07-7
反应条件:1.1 Solvents: Dichloromethane; 1 H,Rt2.1 Reagents: Sodium Thiophenolate Solvents: Dimethylformamide; 3 H,Rt2.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 22.3 Reagents: Sodium Carbonate Solvents: Water; Ph 9; Rt -> 0 °C2.4 Solvents: 1,4-Dioxane; 3 H,0 °C2.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:An Efficient Preparation Of N-Methyl-α-Amino Acids From N-Nosyl-α-Amino Acid Phenacyl Esters
作者:Leggio,Antonella; Et Al
参考文献:Journal Of Organic Chemistry 日期:2010 卷标:75(5) 页码:1386-1392]

59724-75-3 + 70-11-1 = 84000-07-7
反应条件:1.1 Reagents: Cesium Carbonate Solvents: Ethanol; 0 °C; 1 H,Rt1.2 Solvents: Dimethylformamide; 1 H,Rt2.1 Solvents: Dichloromethane; 1 H,Rt3.1 Reagents: Sodium Thiophenolate Solvents: Dimethylformamide; 3 H,Rt3.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 23.3 Reagents: Sodium Carbonate Solvents: Water; Ph 9; Rt -> 0 °C3.4 Solvents: 1,4-Dioxane; 3 H,0 °C3.5 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:An Efficient Preparation Of N-Methyl-α-Amino Acids From N-Nosyl-α-Amino Acid Phenacyl Esters
作者:Leggio,Antonella; Et Al
参考文献:Journal Of Organic Chemistry 日期:2010 卷标:75(5) 页码:1386-1392

N-Fmoc-N-Methyl-L-Alanine Benzhydyl Ester置于三氟乙酸体系中,用二氯甲烷,甲苯作为反应溶剂,化学反应 1.0H,以96%的收率获得产物fmoc-N-甲基-L-丙氨酸
参考文献:N-Fmoc-N-甲基-α-氨基酸和n-糖基-N-甲基-α-氨基酸的制备
标题:N-Fmoc-N-甲基-α-氨基酸和n-糖基-N-甲基-α-氨基酸的制备
摘要:亲脂性n-Fmoc-N-甲基-α-氨基酸和n-糖基-N-甲基-α-氨基酸(用于制备n-甲基化肽的有趣结构单元)的合成简便途径是提出了.nosyl和fmoc保护的单体都是可及的,因此这些化合物可用于溶液以及固相肽合成中.该方法是基于使用苯甲基来暂时保护n-糖基-α-氨基酸的羧基功能以及随后n的甲基化-重氮基的-Nosyl-α-氨基酸二苯甲基酯.苯甲基酯具有几个有益的特征,例如制备简单,对甲基化的稳定性以及在温和条件下的选择性脱保护.整个过程非常有效,因为所采用的条件保持了氨基酸前体的手性完整性,并且该过程不需要对甲基化产物进行色谱纯化.
DOI:10.1007/s00726-008-0221-8

海关参考信息

2902600000-乙苯
2905121000-正丙醇
2912110000-甲醛
2912120000-乙醛
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-2023272006-A1
优先权日:2021-08-31
标题:Peptidomimetics and method of synthesis thereof
发明人：NEFZI ADEL
权利人:NEFZI ADEL; THE FLORIDA INTERNATIONAL UNIV BOARD OF TRUSTEES
摘要:The subject invention provides compounds, peptidomimetics, and methods of synthesis thereof. The subject invention provides the synthesis and use of guanidino acids and/or poly guanidino acids not only as vehicles for drug delivery but as toolbox for drug discovery. The peptidomimetic of the subject invention comprises oligo(guanidino acid)s or poly(guanidino acid)s with guanidines as peptide bond surrogates. The incorporation of the guanidine as amide bond surrogates offers significant differences in polarity, hydrogen bonding capability, and acid-base character.

专利号:US-2023391818-A1
优先权日:2020-11-05
标题:Peptide synthesis method for suppressing defect caused by diketopiperazine formation
发明人：NOMURA KENICHI; KAGE MIRAI; TAMIYA MINORU; KANAZAWA JUNICHIRO
权利人:CHUGAI PHARMACEUTICAL CO LTD
摘要:Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.

专利号:CN-104284891-A
优先权日:2012-03-17
标题:Conformational Restricted Total Synthesis of Macrocyclic Compounds

专利号:US-10017481-B2
优先权日:2012-03-17
标题 :Conformationally constrained, fully synthetic macrocyclic compounds
发明人：OBRECHT DANIEL; ERMERT PHILIPP; OUMOUCH SAID; PIETTRE ARNAUD; GOSALBES JEAN-FRANÃ‡OIS; THOMMEN MARC
权利人:POLYPHOR AG
摘要:The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

专利号:US-2024124517-A1
优先权日:2020-12-25
标题:Method for producing peptide compound containing n-substituted-amino acid residue
发明人：MORITA YUYA; NOMURA KENICHI
权利人:CHUGAI PHARMACEUTICAL CO LTD
摘要:An object of the present invention is to provide a method for efficiently producing a high-purity peptide compound with a high yield. It has been found that the object can be achieved by supporting a peptide on a solid phase synthesis resin prior to a first elongation reaction in a solid phase process.

专利号:US-12331072-B2
优先权日:2018-11-30
标题 :Deprotection method and resin removal method in solid-phase reaction for peptide compound or amide compound, and method for producing peptide compound
发明人：IWASAKI KOTARO; KOMIYA SHIO
权利人:CHUGAI PHARMACEUTICAL CO LTD
摘要:The present inventors found that peptide compounds/amide compounds in which the protecting groups of interest are removed and/or which are removed from resins for solid-phase synthesis can be produced without main chain damage by contacting starting peptide compounds/amide compounds with silylating agents.