CAS: 186023-49-4; (S)-3-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)-L-Valyl)-2,2-Dimethyloxazolidine-4-Carboxylic Acid

该化合物是一种合成化合物,通常用于peptide化学,特别是固相丙酸合成."Fmoc"(9-氟甲基乙氧碳基)组群是氨基酸氨基终点的保护组,允许有选择的反应,而不会干扰其他功能组别.valine(Val)和Serin(Ser)残留物的复合特征对Peptides的结构和功能特性十分重要.加入{psi(Me,Me)pro}modity 表示一种经修改的pline结构,它能够影响所产生的peptide的兼容性和稳定性.这种修改通常用于提高peptide的生物活性或溶性.该化合物的典型特征是其分子重量,有机溶剂的溶解性以及各种条件下的稳定性.其应用范围扩大到药物设计,分子生物学以及基于peptide的治疗方法在实验室环境中的研制和开发基本防范措施.在各种合成化合物使用期间,其基本处理过程中,这些是各种合成化合物.

英文名称(S)-3-((((9H-Fluoren-9-yl)Methoxy)Carbonyl)-L-Valyl)-2,2-Dimethyloxazolidine-4-Carboxylic Acid
中文名称(4S)-3-[(2S)-2-[[芴甲氧羰基]氨基]-3-甲基-1-氧代丁基]-2,2-二甲基-4-恶唑烷羧酸
IUPAC名称(S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)-L-valyl)-2,2-dimethyloxazolidine-4-carboxylic acid
其它别名(4S)-3-[(2S)-2-[[(9H-Fluoren-9-Ylmethoxy)Carbonyl]Amino]-3-Methyl-1-Oxobutyl]-2,2-Dimethyl-4-Oxazolidinecarboxylic Acid; Fmoc-Val-Ser(Psime,Mepro)-Oh; Fmoc-L-Val-L-Ser[psi(Me,Me)Pro]-Oh; (S)-3-[n-(9-Fluorenylmethyloxycarbonyl)-L-Valinyl]-2,2-Dimethyloxazolidine-4-Carboxylic Acid; Fmoc-Val-Ser[psi(Me,Me)Pro]-Oh≥ (Hplc); Fmoc-Val-Ser[ψ(Me,Me)Pro]-Oh; (9H-Fluoren-9-yl)Methoxy]Carbonyl Val-Serpsi(Me,Me)Pro-Oh
CAS编号186023-49-4
MFCD编号:MFCD18427720
分子式:C26H30N2O6分子量:466.53
产品CID: 949582
产品分类化学试剂 → 有机试剂 → 多环化合物

相似结构搜索
InChIKey: KLYUTTJBDDHKOC-VXKWHMMOSA-N
KLYUTTJBDDHK°C-VXKWHMMOSA-N
计算化学: 氢键受体数6.0氢键供体数2.0可旋转键数7.0

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-P280-P301+P312-P302+P352-P305+P351+P338
WGK GermanyWGK 2 water endangering

上下游产品

(S)-3-[(S)-2-(9H-Fluoren-9-Ylmethoxycarbonylamino)-3-Methyl-Butyryl]-2,2-Dimethyl-Oxazolidine-4-Carboxylic Acid Benzyl Ester 186023-48-3
L-丝氨酸,N-[(9H-芴-9-基甲氧基)羰基]-L-缬氨酰-,苯基甲基酯 Fmoc-Val-Ser-Obn 186023-39-2

合成工艺路线路线简述

合成目标产物 Fmoc-Val-Ser(Psime,Mepro)-Oh 主要起始原料 L-Serine, N-[(9H-Fluoren-9-Ylmethoxy)Carbonyl]-L-Valyl-, Phenylmethyl Ester
(文献来源)合成步骤主要原料 L-Serine, N-[(9H-Fluoren-9-Ylmethoxy)Carbonyl]-L-Valyl-, Phenylmethyl Ester

📜L-丝氨酸,N-[(9H-芴-9-基甲氧基)羰基]-L-缬氨酰-,苯基甲基酯置于palladium On Activated Charcoal 氢气,4-甲基苯磺酸吡啶体系中,用甲醇,N,N-二甲基甲酰胺,甲苯用作溶剂,化学反应 15.0H,反应生成(4S)-3-[(2S)-2-[[芴甲氧羰基]氨基]-3-甲基-1-氧代丁基]-2,2-二甲基-4-恶唑烷羧酸
参考文献:Pseudo-Prolines As A Molecular Hinge: Reversible Induction Of Cis Amide Bonds Into Peptide Backbones
标题:Pseudo-Prolines As A Molecular Hinge: Reversible Induction Of Cis Amide Bonds Into Peptide Backbones
摘要:Serine,Threonine-Derived (4S)-Oxazolidine-4-Carboxylic Acid,And Cysteine-Derived (4R)-Thiazolidinecarboxylic Acid,Denoted Pseudo-Proline (Xaa[psi(R1,R2)Pro]),Serve As Structure Disrupting,Solubilizing Building Blocks In Peptide Synthesis. Variation Of The 2-C Substituents Within The Heterocyclic System Results In Different Physicochemical And Conformational Properties. NMR Studies Of A Series Of Pseudo-Proline (Psi Pro)-Containing Peptides Reveal A Pronounced Effect Of The 2-C Substituents Upon The Cis To Trans Ratio Of The Adjacent Amide Bond In Solution. 2-C Unsubstituted Systems Show A Preference Similar To That Of The Proline Residue For The Trans Form,Whereas 2,2-Dimethylated Derivatives Adopt The Cis Amide Conformation In High Content. For 2-Monosubstituted Psi Pro,The Cis-Trans Distribution Depends On The 2-C Chirality. For The 2-(S)-Diastereoisomer,Both Forms Are Similarly Populated In Solution,Whereas The 2-(R)-Epimer Adopts Preferentially The Trans Form. The Results Are Supported By Conformational Energy Calculations And Suggest That,By Tailoring The Degree Of Substitution,Pseudo-Prolines May Serve As A Temporary Proline Mimetic Or As A Hinge In Peptide Backbones.
Doi:10.1021/ja962780A