Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fmoc (SO3H) protected amino acid having excellent hydrophilicity and preparation method thereof

A technology of SO3H and amino acids, which is applied in the field of preparation and purification of Fmoc-protected amino acids with good hydrophilicity and its preparation, and can solve the problems of poor hydrophilicity of polypeptides

Inactive Publication Date: 2017-04-05
HYBIO PHARMA
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The purpose of the present invention is to effectively increase the hydrophilicity of the polypeptide, thereby effectively solving the problems of poor solubility of amino acids in liquid phase synthesis and poor hydrophilicity of polypeptides in the purification process

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fmoc (SO3H) protected amino acid having excellent hydrophilicity and preparation method thereof
  • Fmoc (SO3H) protected amino acid having excellent hydrophilicity and preparation method thereof
  • Fmoc (SO3H) protected amino acid having excellent hydrophilicity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of 9-((chlorocarbonyloxy)methyl)-9H-fluorene-2-sulfonic acid

[0033] Fluorenylmethoxycarbonyl chloride (64.75g) was dissolved in dichloromethane (500ml), and cooled to 0°C. A dichloromethane solution of methanesulfonyl chloride was slowly added dropwise (14 mL of methanesulfonyl chloride was dissolved in 250 mL of dichloromethane), and the temperature was controlled not to exceed 10° C. After the dropwise addition, stirring was continued for 3 hours. Cyclohexane (500 mL) was added to the reaction liquid. The reaction solution was centrifuged, and the obtained solid was washed three times with a mixed solvent (dichloromethane:cyclohexane=1:1, 750 mL×3) to obtain an off-white solid.

[0034] Structural data:

[0035] h 1 NMR: (D 3 COD)64.2-4.5(m,3,CHCH 2 ),5.4(s,H 2 O / RS0 3 H),7.1-7.9(m,6,aryl),8.1(s,1,H-1aryl)

Embodiment 2

[0036] Embodiment 2: the preparation of L-alanine benzyl ester

[0037] Dissolve L-alanine (3.5g) and p-toluenesulfonic acid (8.2g) in benzyl alcohol (16ml), add benzene (8ml) to the reaction solution, raise the temperature of the system to 100°C, reflux the benzene with water for about 15h. After the reaction solution was cooled to room temperature, diethyl ether (15 ml) was added, and then placed in the refrigerator overnight. Filtration afforded a white solid. The white solid was crystallized from acetone. The obtained crystals were dissolved in dichloromethane, washed three times with 5% aqueous sodium bicarbonate solution (20 mL×3), dried the organic phase with anhydrous sodium sulfate, filtered, and spun to remove the solvent to obtain a colorless oil.

Embodiment 3

[0038] Example 3: N-(9-(2-sulfonic acid)-fluorenylmethoxycarbonyl)-L-alanine benzyl ester

[0039]The product 9-((chlorocarbonyloxy)methyl)-9H-fluorene-2-sulfonic acid (7.6g) obtained in Example 1 was dissolved in a mixed solvent of ethyl acetate (10mL) and dichloromethane (150mL) . In addition, L-alanine benzyl ester (4 g) was weighed and dissolved in a mixed solvent of dichloromethane (100 mL) and pyridine (50 mL), and cooled to 0° C. in an ice bath. Slowly add the 9-((chlorocarbonyloxy)methyl)-9H-fluorene-2-sulfonic acid solution dropwise into the L-alanine benzyl ester solution, keeping the temperature below 10°C. After the dropwise addition, react at room temperature until no raw material remains as detected by TLC (ninhydrin color development). Aqueous citric acid (10%) was added to the reaction liquid to wash three times, the organic phase was spin-dried, the residue was dissolved in dichloromethane, and washed three times with water. The organic phase was dried over...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to an amino acid protective group and particularly relates to a purified Fmoc (SO3H) protected amino acid having excellent hydrophilicity and a preparation method thereof. A main structure of the Fmoc (SO3H) protected amino acid is represented as the chemical formula II, wherein R is the side chains of alanine (Ala), valine (Val), leucine (Leu), isoleucine (Ile), proline (Pro), phenylalanine (Phe), tryptophan (Trp), methionine (Met), glycine (Gly), serine (Ser), threonine (Thr), cysteine (Cys), tyrosine (Tyr), asparagines (Asn), glutamine (Gln), lysine (Lys), arginine (Arg), histidine (His), aspartic acid (Asp) or glutamic acid (Glu).

Description

technical field [0001] The invention relates to an amino acid protecting group, in particular to a Fmoc(SO 3 H) Protected amino acids and methods for their preparation. Background technique [0002] In recent years, the solid-phase peptide synthesis technology using the Fmoc protection strategy has been widely used. However, missing peptides and unwanted short peptide impurities are formed due to incomplete linkage or chain termination conditions in the peptide synthesis. Therefore, in order to improve the purity of the polypeptide, the purification of the polypeptide is particularly important. People have also improved the purity of polypeptides by various methods. [0003] However, in the process of preparing and purifying peptides in high performance liquid phase, some peptides are very difficult to prepare and purify due to their poor hydrophilicity, which has also become a problem often faced in peptide purification. Therefore, the present invention inserts Fmoc(SO ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C303/22C07C309/43C07D209/26C07K1/06C07K1/04
CPCY02P20/55
Inventor 陶志强刘飞孟宓鹏程陶安进袁建成
Owner HYBIO PHARMA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com