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4-Bromo-D-phenylalanine typically exists in the form of white to almost white crystalline solids. The molecular formula is C9H10BrNO2, CAS 62561-74-4, which contains benzene ring, alanine group, and bromine atom. Soluble in some organic solvents, such as methanol, ethanol, and dichloromethane. The solubility in water is relatively low. It is a chiral molecule and belongs to the D-stereoisomer. It has optical rotation properties and can cause polarized light to undergo optical rotation. In addition to being used for synthesizing peptide and protein drugs, it can also be used for synthesizing peptide solid-phase synthesis reagents. These reagents can be used to connect amino acids in solid-phase synthesis, thereby preparing various peptide solid-phase synthesis reagents. These reagents can be used to study the structure and function of peptides and proteins, as well as to study the interactions between peptides and proteins.
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Chemical Formula |
C9H10BrNO2 |
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Exact Mass |
243 |
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Molecular Weight |
244 |
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m/z |
243 (100.0%), 245 (97.3%), 244 (9.7%), 246 (9.5%) |
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Elemental Analysis |
C, 44.29; H, 4.13; Br, 32.74; N, 5.74; O, 13.11 |
4-Bromo-D-phenylalanine is a compound with important uses, and the following are all its uses:
It is a commonly used amino acid analogue that can be used to synthesize peptide and protein drugs. It has similar chemical properties and structure to natural amino acids, making it an effective substitute. By introducing 4-Bromo-D phenylalanine into peptide or protein drugs, the biological activity and pharmacokinetic properties of the drug can be improved, thereby improving its efficacy and reducing side effects.
4-Bromo-D phenylalanine is often used as a building block in the synthesis of peptide and protein drugs, and can be used to synthesize drugs with specific structures and functions. These drugs can be used to treat various diseases, such as cancer, neurological diseases, metabolic diseases, autoimmune diseases, etc. By introducing 4-Bromo-D phenylalanine into these drugs, their water solubility and stability can be improved, thereby improving the efficacy of the drug and reducing side effects.
2. Used to study protein structure:
4-Bromo-D phenylalanine can be used to study protein structure. Due to its chemical properties similar to natural amino acids, it can be used to prepare protein mutants to study the structural and functional relationships of proteins. By introducing 4-Bromo-D phenylalanine into proteins, the structure and properties of proteins can be altered, thereby affecting their biological function and activity. This technology has been widely applied in the study of the structure and function of various proteins.
In studying protein structure, 4-Bromo-D phenylalanine is often used as a marker that can be used to label specific sites in proteins. By introducing 4-Bromo-D phenylalanine into specific sites in proteins, the structure and kinetic processes of proteins can be studied. In addition, in studying protein structure, 4-Bromo-D phenylalanine can also be used to prepare antigens and antibodies for studying molecular recognition processes in immunology and biology.
3. Used for synthesizing fluorescent probes:
4-Bromo-D phenylalanine can be used to synthesize fluorescent probes. Due to its bromine atom, fluorescent groups can be introduced into the probe to prepare probes with fluorescent properties. These fluorescent probes can be used to detect small molecules and proteins in biological systems, as well as to study the interactions and dynamic processes of biological molecules.
Fluorescent probes are one of the commonly used tools in biology and medicine, which can be used to study the biological processes of cells and tissues. By introducing 4-Bromo-D phenylalanine into the fluorescent probe, a fluorescent signal probe with specific wavelength and intensity can be prepared. These fluorescent probes can be used to detect specific molecules and proteins in biological systems, and to study their localization, interactions, and dynamic processes. In addition, fluorescent probes can also be used in cell imaging and tracing studies to study the biological processes of cells and tissues.
4. Used for synthesizing non natural amino acid analogues:
4-Bromo-D phenylalanine can be used to synthesize non natural amino acid analogues. By reacting with appropriate reagents, a series of unnatural amino acid analogues containing different functional groups can be prepared. These compounds can serve as effective candidates for drug molecules and functional materials, for the treatment of diseases and the development of new performance materials.
Non natural amino acid analogues are an important research direction in modern organic chemistry and new material science. By introducing 4-Bromo-D phenylalanine into these analogues, a compound with a specific structure and function can be prepared. These compounds can serve as effective candidates in the fields of drug molecules, catalysts, optoelectronic materials, self-assembled membranes, etc., for applications such as treating diseases, catalyzing chemical reactions, and developing new performance materials.
5. Used for synthesizing pesticides and herbicides:
4-Bromo-D-phenylalanine can be used to synthesize pesticides and herbicides. It can be used as a block to synthesize circular structures in various pesticide and herbicide molecules. These pesticides and herbicides can be used to control plant diseases, pests, and weeds, improving crop yield and quality.
Pesticides and herbicides are one of the commonly used chemicals in agriculture, which can be used to control plant diseases, pests, and weeds, improve crop yield and quality.
By introducing 4-Bromo-D phenylalanine into pesticide and herbicide molecules, their chemical properties, biological activity, and efficacy can be improved, leading to the development of a more effective pesticide or herbicide. In addition, 4-Bromo-D phenylalanine can also be used to prepare insecticides and other agricultural chemicals to control the reproduction and growth of pests and protect crops.
4-Bromo-D phenylalanine is a compound with important applications, and its common synthesis methods include the following two:
Method 1:
The synthesis route of this method is to use acetophenone as the raw material, and obtain 4-bromo-D phenylalanine through bromination, amination, and resolution. The specific steps are as follows:
Dissolve acetophenone in dry carbon tetrachloride, slowly introduce bromine under cooling and stirring conditions, and control the temperature below 10 ℃.
Br2 + C6H5COCH3 → C6H5COCH2Br
After the bromination reaction is completed, a potassium hydroxide solution is added and the temperature is controlled between 0 and 10 ℃ for nucleophilic substitution reaction to obtain 4-bromophenone.
C6H5COCH2Br + KOH → C6H5COCH2COOK
Dissolve 4-bromophenyl ethyl ketone in anhydrous ethanol and add sodium hydroxide solution for esterification reaction to obtain 4-bromophenyl ethyl acetate.
C6H5COCH2COOK + CH3CH2OH → C6H5COCH2COOC2H5 + KOH
Dissolve ethyl 4-bromophenylacetate in a methanol solution of sodium methoxide for alcoholysis reaction to obtain methyl 4-bromophenylpropionate.
C6H5COCH2COOC2H5 + CH3OH + CH3ONa → C6H5COCH2COOCH3 + NaBr + NaOH
Hydrolysis reaction was carried out between methyl 4-bromophenylpropionate and sodium carbonate aqueous solution at 70 ℃ to obtain sodium 4-bromophenylpropionate.
C6H5COCH2COOCH3 + Na2CO3 → C6H5COCH2COONa + CH3COONa
4-bromophenylalanine was obtained by neutralizing 4-bromophenylalanine sodium with hydrochloric acid at 80 ℃.
C6H5COCH2COONa + HCl → C6H5CH(Br)COOH + NaCl
Crystallize 4-bromophenylalanine with hydrobromic acid to obtain high-purity 4-bromo-D-phenylalanine.
C6H5CH(Br)COOH + HBr → C6H5CH(Br)COO(-)Br(+)
The advantages of this method are easy availability of raw materials, simple steps, mild reaction conditions, high yield, and good product quality.
Method 2:
The synthesis route of this method is based on chiral ring α- Amino alcohol is used as the raw material to obtain 4-bromo-D phenylalanine through bromination, amination, and resolution. The specific steps are as follows:
1. Chiral ring α- Chirality generated by the reaction of amino alcohols with phosphorus tribromide α- Brominated alcohols:
Br2 + CH(OH)R → CH(OH)RBr
2. Chirality α- Chirality generated by the reaction of brominated alcohols with potassium hydroxide α- Potassium bromate:
CH(OH)RBr + KOH → CH(OH)RK + Br(-)K(+)
3. Chirality α- Chirality generated by the reaction of potassium bromate with ethanol α- Brominated esters:
CH(OH) RK + CH3CH2OH → CH(OH)RCOOC2H5 + KOH
4. Chirality α- Reaction of Brominated Esters with Ammonium Chloride to Produce Chirality α- Amino acid esters:
CH(OH)RCOOC2H5 + NH4Cl → CH(OH)RNHCOOC2H5 + HCl
5. Chirality α- Chirality generated by the reaction of amino acid esters with sodium carbonate α- Amino acids:
CH(OH)RNHCOOC2H5 + Na2CO3 → CH(OH)RNHCOONa + CO3Na
6. Chirality α- Chirality generated by the reaction of amino acids with hydrochloric acid α- Amino alcohol:
CH(OH)RNHCOONa + HCl → CH(OH)RNH2 + NaCl
7. Chirality α- Chirality generated by the reaction of amino alcohols with hydrobromic acid α- Brominated alcohols:
CH(OH)RNH2 + HBr → CH(OH)RNHBr
8. Chirality α- Chirality generated by the reaction of brominated alcohols with sodium hydroxide α- Hydroxyl acid:
CH(OH)RNHBr + NaOH → CH (OH)RCOONa + NHBr(-)Na(+)
9. Chirality α- Reaction of Hydroxyl Acids with Hydrochloric Acid to Produce High Purity Chirality α- Hydroxyl acid:
CH(OH)RCOONa + HCl → CH(OH)RCOOH + NaCl
10. Chirality α- Hydroxyl acid reacts with hydrobromic acid to produce high-purity 4-bromo-D phenylalanine:
CH(OH)RCOOH + HBr → C6H5CH(Br)COOH
The advantages of this method are high selectivity, high product purity, and good resolution effect, but the raw material cost is high.
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