Hydroxybenzotriazole
Encyclopedia
Hydroxybenzotriazole is an organic compound
that is a derivative of benzotriazole. It is mainly used to suppress racemization and improve the efficiency of peptide synthesis
. It is a white crystalline powder. Commercial HOBt always contains some water (~11.7% wt as the HOBt monohydrate crystal) because anhydrous HOBt is explosive.
involves the condensation of the amino group of protected amino acid
s with the activated ester. HOBt is used to produce such activated esters. These esters are insoluble (like the N-hydroxysuccinimide
esters) and react with amines at ambient temperature to give amides.
HOBt is also used for the synthesis of amides from carboxylic acid
s aside from amino acids. These substrates may not be convertable to the acyl chloride
s. For instance amide derivatives of ionophoric
antibiotics have been prepared in this way.
Together with laccase
, HOBt is also used for bleaching pulps. The method is still on the experimental stage and have yet not been commercialized.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
that is a derivative of benzotriazole. It is mainly used to suppress racemization and improve the efficiency of peptide synthesis
Peptide synthesis
In organic chemistry, peptide synthesis is the production of peptides, which are organic compounds in which multiple amino acids are linked via amide bonds which are also known as peptide bonds...
. It is a white crystalline powder. Commercial HOBt always contains some water (~11.7% wt as the HOBt monohydrate crystal) because anhydrous HOBt is explosive.
Use in peptide synthesis
Automated peptide synthesisPeptide synthesis
In organic chemistry, peptide synthesis is the production of peptides, which are organic compounds in which multiple amino acids are linked via amide bonds which are also known as peptide bonds...
involves the condensation of the amino group of protected amino acid
Amino acid
Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...
s with the activated ester. HOBt is used to produce such activated esters. These esters are insoluble (like the N-hydroxysuccinimide
N-Hydroxysuccinimide
N-Hydroxysuccinimide is a compound with a molecular weight of 115.09 and a melting point of 95 °C.As it is slightly acidic, it is an irritant to skin, eyes and mucous membranes....
esters) and react with amines at ambient temperature to give amides.
HOBt is also used for the synthesis of amides from carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...
s aside from amino acids. These substrates may not be convertable to the acyl chloride
Acyl chloride
In organic chemistry, an acyl chloride is an organic compound with the functional group -CO-Cl. Their formula is usually written RCOCl, where R is a side chain. They are usually considered to be reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride,...
s. For instance amide derivatives of ionophoric
Ionophore
An ionophore is a lipid-soluble molecule usually synthesized by microorganisms to transport ions across the lipid bilayer of the cell membrane...
antibiotics have been prepared in this way.
Together with laccase
Laccase
Laccases are copper-containing oxidase enzymes that are found in many plants, fungi, and microorganisms. The copper is bound in several sites; Type 1, Type 2, and/or Type 3. The ensemble of types 2 and 3 copper is called a trinuclear cluster . Type 1 copper is available to action of solvents,...
, HOBt is also used for bleaching pulps. The method is still on the experimental stage and have yet not been commercialized.