CAS: 86123-10-6; Fmoc-D-Phe-Oh

该化合物是氨酸苯丙胺的衍生物,其特点是存在9氟甲基苯丙胺碳酸(Fmoc)保护组,该化合物通常用于peptide合成,特别是固相聚聚硫化物合成(SPS),因为它有能力保护氨酸的氨基组,同时允许进一步的反应.Fmoc-D-Phenylaline通常是白到白的固体,在二甲基成份和二甲基硫氧化(DMSO)等有机溶剂中溶解,但在水中溶解程度较低.Fmoc组可以在基本条件下被清除,这有利于将保护氨酸与其他氨基酸结合到丙酸链中的氨基酸中.苯丙胺的D-conformation表明,自然蛋白中通常没有找到的对等离子,因此它有助于研究生物化学系统中具有生命力的化学-化学化学场的影响.

英文名称Fmoc-D-Phe-Oh
中文名称Fmoc-D-苯丙氨酸
IUPAC名称(((9H-fluoren-9-yl)methoxy)carbonyl)-D-phenylalanine
其它别名N9芴甲氧羰基d苯丙氨酸
CAS编号86123-10-6
MFCD编号:MFCD00062955
EINECS号:630-426-8
FDA UNII编号:S98AJ2BS3A
分子式:C24H21NO4
分子量:387.43
产品CID: 1861794
产品分类有机原料→生命科学→氨基酸及其衍生物→苯丙氨酸及其衍生物

相似结构搜索
InChIKey: SJVFAHZPLIXNDH-JOCHJYFZSA-M
InChI=1S/C24H21NO4/c26-23(27)22(14-16-8-2-1-3-9-16)25-24(28)29-15-21-19-12-6-4-10-17(19)18-11-5-7-13-20(18)21/h1-13,21-22H,14-15H2,(H,25,28)…
计算化学: 氢键受体数3.0氢键供体数2.0可旋转键数6.0

相似化合物

126727-04-6 1161-13-3 13734-34-4

物理性质

熔点181-185°C
沸点620.1°C at 760 mmHg
闪点328.8±30.1 °C
密度1.3±0.1 g/cm3
pKa:3.77±0.10(预测)
PSA:75.63
LogP:4.221
折射率1.633
蒸汽压0.0±1.9 mmHg at 25°C
溶解性Soluble In Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,Etc.
敏感性按规定使用和贮存的不会分解，避氧化物、潮湿
外观形态白色粉末或结晶粉末
储存条件2-8°C
产品应用该化合物用作合成手性药物和生物活性分子的分子脚架;它也与合成受管制物质----苯丙胺衍生物有关,因此禁止销售.

MSDS等安全信息

GHS符号GHS07
警示词Warning
危险描述H302-H315-H319-H335
防范说明P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
UN编号NONH for all modes of transport
危险品标志Xi
安全声明22-24/25
WGK Germany3

上下游产品

合成工艺路线路线简述

合成目标产物 Fmoc-D-Phenylalanine 主要起始原料 9-Fluorenylmethyl Chloroformate
63-91-2 + 1023867-12-0 = 86123-10-6
反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetonitrile,Water; Overnight,Rt1.2 Reagents: Hydrochloric Acid; Ph 2
标题:Synthesis Of Carboxylic Acids,Esters,And Amides From 1,1-Dibromoalkenes Via Oxidation Of Alkynyl Boronate Intermediates
作者:Tao,Lei; Et Al
参考文献:Chemistryselect 日期:2021 卷标:6(33) 页码:8532-8536]

= 86123-10-6
反应条件:1.1 Reagents: Sulfuric Acid Solvents: 1,4-Dioxane,Water
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

28920-43-6 + 673-06-3 = 86123-10-6
反应条件:1.1 Reagents: Diisopropylethylamine Solvents: 1,4-Dioxane
标题:Application Of Metal-Free Triazole Formation In The Synthesis Of Cyclic Rgd-Dtpa Conjugates
作者:Van Berkel,Sander S.; Et Al
参考文献:Chembiochem 日期:2008 卷标:9(11) 页码:1805-1815]

28920-43-6 + 673-06-3 = 86123-10-6
反应条件:1.1 Reagents: Sodium Carbonate Solvents: Tetrahydrofuran,Water; 10 Min,0 °C; 2 H,0 °C1.2 Reagents: Hydrochloric Acid Solvents: Water; Acidified
标题:Structure-Based Design Of Pseudopeptidic Inhibitors For Sirt1 And Sirt2
作者:Huhtiniemi,Tero; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:2011 卷标:54(19) 页码:6456-6468]

82911-69-1 = 86123-10-6
反应条件:1.1 Reagents: 2-Iodoxybenzoic Acid Solvents: Methanol1.2 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt2.1 Reagents: Trifluoroacetic Acid; 12 Min,110 °C
标题:Convenient Synthetic Route To An Enantiomerically Pure Fmoc α-Amino Acid
作者:Taber,Douglass F.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(23) 页码:9334-9339]

101023-15-8 + 98-88-4 = 86123-10-6
反应条件:1.1 Reagents: Triethylamine Catalysts: Titanium Tetrachloride Solvents: Acetonitrile; Overnight,Rt2.1 Reagents: 4-Acetamidobenzenesulfonyl Azide,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile; 10 Min,0 °C; 3 H,35 °C3.1 Reagents: Rhodium,Tetrakis[μ-(Octanoato-Ko:Ko′)]Di-,(Rh-Rh) Solvents: Diethyl Ether; 10 Min,Rt -> 45 °C; 3 H,45 °C4.1 Reagents: 2-Iodoxybenzoic Acid Solvents: Methanol4.2 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt5.1 Reagents: Trifluoroacetic Acid; 12 Min,110 °C
标题:Convenient Synthetic Route To An Enantiomerically Pure Fmoc α-Amino Acid
作者:Taber,Douglass F.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(23) 页码:9334-9339]

28920-43-6 + 673-06-3 = 86123-10-6
反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt -> 0 °C; 5 Min,0 °C; 7 H,Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2
标题:Mechanistic Insights Into The Slow Peptide Bond Formation With D-Amino Acids In The Ribosomal Active Site
作者:Melnikov,Sergey V.; Et Al
参考文献:Nucleic Acids Research 日期:2019 卷标:47(4) 页码:2089-2100]

28920-43-6 + 170899-07-7 = 86123-10-6
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water1.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

1086452-13-2 = 86123-10-6
反应条件:1.1 Reagents: Trifluoroacetic Acid; 12 Min,110 °C
标题:Convenient Synthetic Route To An Enantiomerically Pure Fmoc α-Amino Acid
作者:Taber,Douglass F.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(23) 页码:9334-9339]

126727-04-6 = 86123-10-6 [标题:Reaction Conditions
标题:Synergistic Effects On Enantioselectivity Of Zwitterionic Chiral Stationary Phases For Separations Of Chiral Acids,Bases,And Amino Acids By Hplc
作者:Hoffmann,Christian V.; Et Al
参考文献:Analytical Chemistry (Washington 日期:2008 卷标:80(22) 页码:8780-8789]

673-06-3 = 86123-10-6 [标题:Reaction Conditions
标题:Total Synthesis And Stereochemical Assignment Of Sunshinamide And Its Anticancer Activity
作者:Mondal,Joyanta; Et Al
参考文献:Organic Letters 日期:2020 卷标:22(3) 页码:1188-1192]

170115-96-5 = 86123-10-6
反应条件:1.1 Reagents: Diisopropylamine,Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane1.2 -2.1 Reagents: Sodium Hydroxide Solvents: Water2.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

170115-96-5 = 86123-10-6
反应条件:1.1 Reagents: Diisopropylamine,Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane1.2 -2.1 Reagents: Sodium Hydroxide Solvents: Water2.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

620-05-3 + 170115-96-5 = 86123-10-6
反应条件:1.1 Reagents: Diisopropylamine,Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane1.2 -2.1 Reagents: Sodium Hydroxide Solvents: Water2.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

158393-62-5 = 86123-10-6
反应条件:1.1 Reagents: Rhodium,Tetrakis[μ-(Octanoato-Ko:Ko′)]Di-,(Rh-Rh) Solvents: Diethyl Ether; 10 Min,Rt -> 45 °C; 3 H,45 °C2.1 Reagents: 2-Iodoxybenzoic Acid Solvents: Methanol2.2 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt3.1 Reagents: Trifluoroacetic Acid; 12 Min,110 °C
标题:Convenient Synthetic Route To An Enantiomerically Pure Fmoc α-Amino Acid
作者:Taber,Douglass F.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(23) 页码:9334-9339]

185508-77-4 = 86123-10-6
反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Methanol,Water2.1 Reagents: Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane2.2 -3.1 Reagents: Sodium Hydroxide Solvents: Water3.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

4530-20-5 = 86123-10-6
反应条件:1.1 Reagents: Triethylamine,Pivaloyl Chloride Solvents: Dichloromethane1.2 Reagents: Triethylamine2.1 Reagents: Diisopropylamine,Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane2.2 -3.1 Reagents: Sodium Hydroxide Solvents: Water3.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

616-34-2 = 86123-10-6
反应条件:1.1 Catalysts: Butyllithium Solvents: Tetrahydrofuran,Hexane1.2 Solvents: Tetrahydrofuran2.1 Reagents: Diisopropylamine,Butyllithium,Lithium Chloride Solvents: Tetrahydrofuran,Hexane2.2 -3.1 Reagents: Sodium Hydroxide Solvents: Water3.2 -
标题:Highly Practical Methodology For The Synthesis Of D- And L-α-Amino Acids,N-Protected α-Amino Acids,And N-Methyl-α-Amino Acids
作者:Myers,Andrew G.; Et Al
参考文献:Journal Of The American Chemical Society 日期:1997 卷标:119(4) 页码:656-673]

= 86123-10-6
反应条件:1.1 Reagents: 4-Acetamidobenzenesulfonyl Azide,1,8-Diazabicyclo[5.4.0]Undec-7-Ene Solvents: Acetonitrile; 10 Min,0 °C; 3 H,35 °C2.1 Reagents: Rhodium,Tetrakis[μ-(Octanoato-Ko:Ko′)]Di-,(Rh-Rh) Solvents: Diethyl Ether; 10 Min,Rt -> 45 °C; 3 H,45 °C3.1 Reagents: 2-Iodoxybenzoic Acid Solvents: Methanol3.2 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; Rt4.1 Reagents: Trifluoroacetic Acid; 12 Min,110 °C
标题:Convenient Synthetic Route To An Enantiomerically Pure Fmoc α-Amino Acid
作者:Taber,Douglass F.; Et Al
参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(23) 页码:9334-9339

在硫酸体系中,用 1,4-二氧六环,水作为反应溶剂,化学反应 8.0H,以96%的收率获得产物fmoc-D-苯丙氨酸
参考文献:合成 D-和l-α-氨基酸,N-保护的 α-氨基酸和 N-甲基-α-氨基酸的高度实用方法
标题:合成 D-和l-α-氨基酸,N-保护的 α-氨基酸和 N-甲基-α-氨基酸的高度实用方法
摘要:提供了一种非常实用的合成 D-和 L-α-氨基酸,N-保护的 α-氨基酸和 N-甲基-α-氨基酸的方法的完整细节,其中使用伪麻黄碱甘氨酰胺的不对称烷基化作为关键步骤(1) 或伪麻黄碱肌酰胺 (2).介绍了分别从伪麻黄碱和甘氨酸甲酯或肌氨酸甲酯合成 1 和 2 的实用程序.描述了 1 和 2 的烯醇化和随后的烷基化的最佳方案.发现 1 和 2 的烷基化反应对于范围广泛的卤代烷底物非常有效,并且产物以高非对映选择性形成.通过在水或水-二恶烷混合物中加热,这些烷基化反应的产物可以有效地水解并且几乎没有外消旋化.该协议为制备高对映体纯度的无盐 α-氨基酸提供了一种非常实用的方法.或者,烷基化产物...
DOI:10.1021/ja9624073

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-2008287649-A1
优先权日:2006-12-29
标题 :Methods for the synthesis of cyclic peptides
发明人：CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R
权利人:CHEN LIN; HAN YEUN-KWEI; ROBERTS CHRISTOPHER R
摘要:Methods for the synthesis of cyclic peptides are provided, as well as novel dipeptide compounds. The methods include the solid phase synthesis of a dipeptide, which is the coupled to a second peptide in a solid phase reaction. The peptide is then cyclized following the coupling reaction. The methods and dipeptides are particularly useful for the synthesis of MC-4 receptor agonist peptides.

专利号:US-6376649-B1
优先权日:1998-12-18
标题 :Methods for the synthesis of Î±- hydroxy-Î²-amino acid and amide derivatives
发明人：SEMPLE JOSEPH E; LEVY ODILE E
权利人:CORVAS INT INC
摘要:Methods for the synthesis of alpha-hydroxy-beta-amino acid and amide derivatives and alpha-ketoamide derivatives and novel derivatives made by these methods are provided. These methods involve reacting a N-terminally blocked (protected) aminoaldehyde with an isonitrile and a carboxylic acid to give an amino-alpha-acyloxy carboxamide. The acyloxy group may be removed to give the derivative. Alternatively the protecting group is removed and acyl shift occurs to give the derivative. These derivatives are useful in the synthesis of compounds such as peptidyl alpha-ketoamides and alpha-hydroxy-beta-carboxylic acid and amide derivatives. Certain of these compounds have been reported to have activity as inhibitors of proteases, such as serine proteases and cysteine proteases.

专利号:WO-9747313-A1
优先权日:1996-06-10
标题:Total synthesis of bacitracin polypetides
发明人：GRIFFIN JOHN H; MCDOUGAL PATRICK G
权利人:UNIV LELAND STANFORD JUNIOR
摘要:Methods for the total synthesis of bacitracin-type polypeptides are described, as well as useful analogs of bacitracin A, and treatment of bacterial infection using such analogs.

专利号:US-2017320908-A1
优先权日:2014-11-19
标题 :Solid phase synthesis of cyclic amino acid molecules
发明人：HICKEY JENNIFER L; MANCUSO JOHN; MARSAULT ERIC; ROUGHTON ANDREW L; TREDER ADAM P; TREMBLEY MARIE-CLAUDE J; YUDIN ANDREI K; ZARETSKY SERGE
权利人:ENCYCLE THERAPEUTICS; GOVERNING COUNCIL OF THE UNIV OF TORONTO; UNIV SHERBROOKE
摘要:The present invention relates to cyclic amino acid molecules and methods of preparing the same, and in particular the macrocyclization of amino acids or linear peptides bound to a solid support.

专利号:US-9388212-B2
优先权日:2013-02-21
标题:Solid phase peptide synthesis via side chain attachment
发明人：BARLOS KLEOMENIS K
权利人:CHEMICAL & BIOPHARMACEUTICAL LAB OF PATRAS S A
摘要:The present application discloses peptides and peptaibols of high purity may be obtained by solid phase peptide synthesis using as the starting resin hydroxy amino acids, hydroxy amino acid amides, hydroxy amino alcohols or small peptides containing hydroxy amino acids attached to polymers through their side chain.

专利号:US-7951905-B2
优先权日:2006-09-18
标题 :Synthesis of carbohydrate-templated amino acids and methods of using same
发明人：SCHWEIZER FRANK; ZHANG KAIDONG; OWENS NEIL; ZHANEL GEORGE
权利人:UNIV MANITOBA
摘要:The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

其他信息查阅

四川同晟氨基酸有限公司

网址: www.biots.cn
企业联系电话：0838-2274206/13350585791👤
地址:四川省德阳市天元开发区永定河西路23号

⚠️ 未注册 · 未认证企业

备注: 📌 数据来源说明：本展台内容基于各搜索引擎等公开数据整理，仅作展示用途。请用户自行辨别
✉️ 若企业需抹除展台内容或有异议，请通过页面底部联系方式告知我们，我们会尽快处理。

湖北恒绿源科技有限公司

网址: http://www.hbhlykj.com
企业联系电话：027-88188016👤
地址:湖北省武汉市江岸区黄孝河路182号

⚠️ 未注册 · 未认证企业

中肽生化有限公司

网址: http://www.chinesepeptide.com
电话: 0571-86737118👤

⚠️ 未注册 · 未认证企业

备注: 📌 数据来源说明：本展台内容基于各搜索引擎等公开数据整理，仅作展示用途。请用户自行辨别 ✉️ 若企业需抹除展台内容或有异议，请通过页面底部联系方式告知我们，我们会尽快处理。

常州吉恩药业有限公司

网址: http://www.genchem.cn
企业联系电话：18861157601;18861157609👤
地址:江苏省常州市新北区滨江经济开发区玉龙北路658号

⚠️ 未注册 · 未认证企业

天津科创医药中间体技术生产力促进有限公司

网址: http://www.scipharmacn.com
企业联系电话：022-60116533👤
地址:天津市华苑产业园区(环外)海泰发展六道6号海泰绿色产业基地

⚠️ 未注册 · 未认证企业

第 1 / 1 页

现货

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

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):1793-815.
[参考文献]: Chiara Testa, Et Al. 1,4-Disubstituted-[参考文献]: Ngoc-Duc Doan, Et Al. Solid-Phase Synthesis Of C-Terminal Azapeptides. J Pept Sci. 2015 May;21(5):387-91.

合成参考文献

参考文献:10.1007/s00894-019-4064-x
摘要:Kling RC, Burchardt C, Einsiedel J, Hübner H, Gmeiner P. Structure-based exploration of an allosteric binding pocket in the NTS1 receptor using bitopic NT(8-13) derivatives and molecular dynamics simulations. Journal of Molecular Modeling. 2019 Jun 17;25(7):193. doi: 10.1007/s00894-019-4064-x.
参考文献:10.1021/jm0208828
摘要:Kamionka M, Rehm T, Beisel HG, Lang K, Engh RA, Holak TA. In silico and NMR identification of inhibitors of the IGF-I and IGF-binding protein-5 interaction. J Med Chem. 2002 Dec 19;45(26):5655–60. doi: 10.1021/jm0208828.
参考文献:10.1038/s41596-020-00407-y
摘要:Lindner S, Wängler C, Bailey JJ, Jurkschat K, Bartenstein P, Wängler B, Schirrmacher R. Radiosynthesis of [18F]SiFAlin-TATE for clinical neuroendocrine tumor positron emission tomography. Nat Protoc. 2020 Dec;15(12):3827–43. doi: 10.1038/s41596-020-00407-y.
参考文献:10.1007/978-1-0716-0227-0_13
摘要:Hansford KA, Ziora ZM, Cooper MA, Blaskovich MAT. Solid-Phase Synthesis of Octapeptin Lipopeptides. Methods Mol Biol. 2020;2103():199–213. doi: 10.1007/978-1-0716-0227-0_13.

📝 需求与反馈

📲 手机号 / 邮箱 *

✏️ 问题内容 *

尽可能描述清楚需求与问题信息

CAS: 86123-10-6; Fmoc-D-Phe-Oh

相似化合物

物理性质

MSDS等安全信息

上下游产品

合成工艺路线路线简述

海关参考信息

专利信息

其他信息查阅

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

📌 第三方产品分析报告

主要参考文献

合成参考文献

通知