CAS: 94744-50-0; Fmoc-Aib-Oh

该化合物是一种化学化合物,主要用于丙化物合成,并保护氨酸.该化合物是一个氟基甲基乙基(Fmoc)(Fmoc)组,由于该组在基本条件下具有稳定性并在温和酸性条件下易于去除,因此是一个受欢迎的保护群体.该结构包括一个带一个甲基组的分支侧链,该组有助于其消毒特性.它通常是白色到非白色的固体,在有机溶剂中溶解,如二甲基硫氧化物和二甲基二亚硫化物(DMF),但水中的溶解度较低.由于存在碳箱酸功能组,它能够参与各种化学反应,使其在合成有机化学中具有灵敏度.其化学化学物质编号为94744-50,是这种化合物独有的,便于在化学数据库和文献中识别.

英文名称Fmoc-Aib-Oh
中文名称Fmoc-2-氨基异丁酸
IUPAC名称2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpropanoic acid
其它别名2-({[(9H-Fluoren-9-yl)Methoxy]Carbonyl}Amino)-2-Methylpropanoic Acid; Fmoc-Aib-Oh 2-(Fmoc-Amino)Isobutyric Acid; Fmoc-Aib-Oh; 2-(9H-Fluoren-9-Ylmethoxycarbonylamino)-2-Methylpropanoic Acid; Fmoc-2-Aminoisobutyric Acid; N-F
CAS编号94744-50-0
MFCD编号:MFCD00151913
EINECS号:619-072-5
分子式:C19H19NO4
分子量:325.36
产品CID: 1999694
产品分类有机原料→生命科学→氨基酸及其衍生物→丙氨酸及其衍生物

相似结构搜索
InChIKey: HOZZVEPRYYCBTO-UHFFFAOYSA-N
InChI=1S/C19H19NO4/c1-19(2,17(21)22)20-18(23)24-11-16-14-9-5-3-7-12(14)13-8-4-6-10-15(13)16/h3-10,16H,11H2,1-2H3,(H,20,23)(H,21,22)…
计算化学: 氢键受体数3.0氢键供体数2.0可旋转键数4.0

相似化合物

15030-72-5 30992-29-1 62-57-7

物理性质

熔点182-188°C
沸点544.3°C at 760 mmHg
闪点283.0±25.4 °C
密度1.3±0.1 g/cm3
pKa:3.98±0.10(预测)
PSA:75.63
LogP:3.3883
折射率1.600
蒸汽压0.0±1.5 mmHg at 25°C
溶解性Soluble In Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,Etc.
敏感性易受潮
外观形态白色至几乎白色粉末至晶体
储存条件2-8°C
产品应用该化合物用于使用编码的氨基酸扫描法研究受体-受体和相互作用.

MSDS等安全信息

GHS符号GHS07
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-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

CAS号28920-43-6 芴甲氧羰酰氯(Fm°C-Cl) | CAS号5938-34-1 1-(4-methylphen... | CAS号62-57-7 2-氨基异丁酸 | CAS号920-66-1 六氟异丙醇 | CAS号1072922-73-6 2-(methyl(napht...

合成工艺路线路线简述

合成目标产物 Fmoc-Aib-Oh 主要起始原料 9-Fluorenylmethyl Chloroformate And Aminoisobutyric Acid Hydrochloride
427879-09-2 = 94744-50-0
反应条件:1.1 Catalysts: Ytterbium Triflate Solvents: Nitromethane
标题:Highly Selective Deprotection Of Tert-Butyl Esters Using Ytterbium Triflate As A Catalyst Under Mild Conditions
作者:Sridhar,P. Ramu; Sinha,Surajit; Chandrasekaran,S.
参考文献:Indian Journal Of Chemistry 日期:2002 卷标:(1) 页码:157-160]

62-57-7 + 28920-43-6 = 94744-50-0
反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 10 Min,0 °C1.2 6 H,25 °C
标题:Solid-Phase Synthesis Of Benzimidazole Libraries Biased For Rna Targets
作者:Vourloumis,Dionisios; Takahashi,Masayuki; Simonsen,Klaus B.; Ayida,Benjamin K.; Barluenga,Sofia; Et Al
参考文献:Tetrahedron Letters 日期:2003 卷标:44(14) 页码:2807-2811]

62-57-7 + 82911-69-1 = 94744-50-0
反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 10 Min,0 °C1.2 0 °C; Overnight,Rt1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 3,Rt
标题:Multiple Actions Of H2S-Releasing Peptides In Human β-Amyloid Expressing C. Elegans
作者:Ali,Rafat; Hameed,Rohil; Chauhan,Divya; Sen,Shantanu; Wahajuddin,Muhammad; Et Al
参考文献:Acs Chemical Neuroscience 日期:2022 卷标:13(23) 页码:3378-3388]

62-57-7 + 28920-43-6 = 94744-50-0
反应条件:1.1 Reagents: Hydrochloric Acid Catalysts: Zinc Solvents: Acetonitrile,Water
标题:Zinc Promoted Rapid And Efficient Synthesis Of Fmoc- And Z-α,α-Dialkylamino Acids Under Neutral Conditions
作者:Suresh Babu,Vommina V.; Ananda,Kuppanna
参考文献:Indian Journal Of Chemistry 日期:2001 卷标:(1) 页码:70-74]

62-57-7 + 28920-43-6 = 94744-50-0
反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt; 24 H,Rt
标题:Radical-Mediated Activation Of Esters With A Copper/selectfluor System: Synthesis Of Bulky Amides And Peptides
作者:Matsumoto,Akira; Wang,Zhe; Maruoka,Keiji
参考文献:Journal Of Organic Chemistry 日期:2021 卷标:86(7) 页码:5401-5411]

= 94744-50-0 [标题:Reaction Conditions
标题:Preparation Of Human Glucagon-Like-Peptide-1 Mimics And Their Use In The Treatment Of Diabetes And Related Conditions
参考文献:World Intellectual Property Organization]

62-57-7 + 28920-43-6 = 94744-50-0
反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 0 °C; Overnight,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 1,Rt
标题:Proximity-Induced Reactivity And Product Selectivity With A Rationally Designed Bifunctional Peptide Catalyst
作者:Kinghorn,Michael J.; Valdivia-Berroeta,Gabriel A.; Chantry,Donalee R.; Smith,Mason S.; Ence,Chloe C.; Et Al
参考文献:Acs Catalysis 日期:2017 卷标:7(11) 页码:7704-7708]

934816-82-7 + 94744-50-0 = 94744-50-0
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Methanol,Dichloromethane; 60 Min,Rt; 90 Min,Rt
标题:Method For Producing Peptide Compound Containing N-Substituted-Amino Acid Residue
参考文献:World Intellectual Property Organization]

94744-50-0 = 94744-50-0
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dimethylformamide,Dichloromethane; 2 H,25 °C
标题:Insulinotropic Peptide Synthesis Using Solid And Solution Phase Combination Techniques
参考文献:World Intellectual Property Organization]

94744-50-0 = 94744-50-0
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dichloromethane; 18 H,Rt
标题:Preparation Of N-Biaryl(Hetero)Arylsulphonamide Amino Acid Derivatives As Sphingosine 1-Phosphate Receptor Type 1 Antagonists Useful In The Treatment Of Diseases Mediated By Lymphocytes Interactions
参考文献:World Intellectual Property Organization]

94744-50-0 = 94744-50-0
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: Dimethylformamide,Dichloromethane; 2 H,25 °C
标题:Synthesis Of Insulinotropic Peptides By A Solid And Solution Approach Via Preparation And Coupling Of Several Peptide Fragments And Use Of A Pseudoproline In One Of The Fragments
参考文献:World Intellectual Property Organization]

= 94744-50-0 [标题:Reaction Conditions
标题:Synthesis And Antiproliferative Activity Of Culicinin D Analogues Containing Simplified Ahmod-Based Residues
作者:Stubbing,Louise A.; Kavianinia,Iman; Abbattista,Maria R.; Harris,Paul W. R.; Smaill,Jeff B.; Et Al
参考文献:European Journal Of Medicinal Chemistry 日期:2019 卷标:177 页码:235-246]

= 94744-50-0 [标题:Reaction Conditions
标题:Preparation Of Potent And Efficient Cytotoxic Pentapeptides And Their Antibody Drug Conjugates For Treating Cancer
参考文献:United States]

= 94744-50-0 [标题:Reaction Conditions
标题:Synthesis,Conformational Analysis And Cb1 Binding Affinity Of Hairpin-Like Anandamide Pseudopeptide Mimetics
作者:Di Marzo,Maria; Casapullo,Agostino; Bifulco,Giuseppe; Cimino,Paola; Ligresti,Alessia; Et Al
参考文献:Journal Of Peptide Science 日期:2006 卷标:12(9) 页码:575-591]

= 94744-50-0 [标题:Reaction Conditions
标题:Dna-Binding Ligands From Peptide Libraries Containing Unnatural Amino Acids
作者:Lescrinier,Theo; Hendrix,Chris; Kerremans,Luc; Rozenski,Jef; Link,Andreas; Et Al
参考文献:Chemistry - A European Journal 日期:1998 卷标:4(3) 页码:425-433]

62-57-7 + 88752-28-7 = 94744-50-0
反应条件:1.1 Reagents: Potassium Carbonate Solvents: Acetonitrile; 2 H,Rt
标题:Fmoc-Ophth,The Reagent Of Fmoc Protection
作者:Yoshino,Ryo; Tokairin,Yoshinori; Kikuchi,Mari; Konno,Hiroyuki
参考文献:Tetrahedron Letters 日期:2017 卷标:58(16) 页码:1600-1603

在 Ytterbium(Iii) Triflate体系中,用硝基甲烷作为反应溶剂,化学反应 5.0H,以97%的收率获得产物fmoc-2-氨基异丁酸
参考文献:Sridhar,P. Ramu; Sinha,Surajit; Chandrasekaran,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,2002,Vol. 41,# 1,P. 157-160
标题:Sridhar,P. Ramu; Sinha,Surajit; Chandrasekaran,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,2002,Vol. 41,# 1,P. 157-160

海关参考信息

2902600000-乙苯
2905121000-正丙醇
2912110000-甲醛
2912120000-乙醛
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专利信息

专利号:US-8227571-B2
优先权日:2007-12-11
标题 :Insulinotropic peptide synthesis using solid and solution phase combination techniques
发明人：CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R
权利人:CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R; ROCHE PALO ALTO LLC
摘要:The present invention relates to the preparation of insulinotropic peptides that are synthesized using a solid and solution phase (â€œhybridâ€ ) approach. Generally, the approach includes synthesizing three different peptide intermediate fragments using solid phase chemistry. Solution phase chemistry is then used to add additional amino acid material to the third fragment which is then coupled to the second fragment and then the first fragment in solution. Alternatively, a different second fragment is coupled to the first fragment in the solid phase. Then, solution phase chemistry is then used to add additional amino acid material to a different third fragment. Subsequently, this different third fragment is coupled to the coupled first and different second fragment in the solution phase. The use of a pseudoproline in one of the fragments eases solid phase synthesis of that fragment and also eases subsequent solution phase coupling of this fragment to the other fragments. The present invention is very useful for forming insulinotropic peptides such as GLP-1(7-36) and its natural and non-natural counteparts.

专利号:US-2023220001-A1
优先权日:2020-06-09
标题:Method for synthesis of thioether-containing peptides
发明人：GRUSS HENDRIK; LUTZ CHRISTIAN; SÃœSSMUTH RODERICH; Yao guiyang; KNITTEL CAROLINE; KOSOL SIMONE; MAINZ ANDI
权利人:HEIDELBERG PHARMA RES GMBH
摘要:The present invention relates to a method of formation of a sulphur bridge between tryptophan and cysteine in solid phase peptide synthesis under iodine treatment. The invention also relates to the resulting compounds of the method and their respective use.

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:US-10920258-B2
优先权日:2018-03-09
标题 :Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1
发明人：NUIJENS TIMO; TOPLAK ANA; QUAEDFLIEG PETER JAN LEONARD MARIO
权利人:ENZYPEP B V
摘要:A method for synthesizing a peptide having the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly is disclosed. The method includes enzymatically coupling:n (a) a peptide C-terminal ester or thioester having a first peptide fragment with the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine having a second peptide fragment with the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-Ile-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly; wherein:n X is Ala or an Î±-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain Îµ-amino group or of which Lys the side-chain Îµ-amino group is protected with a protective group or of which Lys the side-chain Îµ-amino group is functionalized with an amino acid or another functional group; and Z is Arg or Lys.

专利号:WO-2023105497-A1
优先权日:2021-12-10
标题:Synthesis of glp-1 analogues
发明人：GODHA ATUL KASTURCHAND; NARAYANASWAMY SATHYA VANGANUR; BHAGYARAJ ARETI VENKATA; BAVADEKAR ASLAM JAHANGIR; LAKSHMANAPPA RUDRESH; NAGOOR SHEIKSYEDALI; MURUGAN RANJITHKUMAR; GADAKH AMOL VASANTRAO; SAMBASIVAM GANESH
权利人:ANTHEM BIOSCIENCES PVT LTD
摘要:The present invention provides a method of preparation of GLP-1 peptides by using different peptide fragments having amino acid sequences SEQ ID NO:1 (Fragment IG), SEQ ID NO:2 (Fragment SG), Fragment BG, SEQ ID NO:3, and SEQ ID NO:4 5 and combinations thereof. The method of preparation is environmentally benign, simple, straightforward, and efficient and provides the end product in high yield and purity. The purification method of the peptides is also described.

专利号:US-9593142-B2
优先权日:2013-12-26
标题 :Aldehyde capture ligation technology for synthesis of amide bonds
发明人：ARORA PARAMJIT S; RAJ MONIKA; WU HUABIN
权利人:ARORA PARAMJIT S; RAJ MONIKA; WU HUABIN; UNIV NEW YORK
摘要:The present invention relates to ligation agents and their use in making an amide ligation product. Methods of making the ligation agents are also disclosed.

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主要参考文献

[参考文献]: Luckose F, Et Al. Effects Of Amino Acid Derivatives On Physical, Mental, And Physiological Activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1065.

合成参考文献

摘要:Zhou, Q.-Q.; Wei, Y.; Lu, L.-Q.; Xiao, W.-J., Science of Synthesis: Photocatalysis in Organic Synthesis, (2018) 1, 178.

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CAS: 94744-50-0; Fmoc-Aib-Oh

相似化合物

物理性质

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