Biomaterial Database

Peptide Hydrazides as Thioester Equivalents for the Chemical Synthesis of Proteins. 2020

Yu Wang, and Yi-Ming Li

School of Food and Biological Engineering, Hefei University of Technology, Hefei, China.

The chemical synthesis of proteins allows for the precise control of structural information at the atomic level, overcoming the limits of protein expression. Peptide hydrazides are widely used as thioester equivalents in the total chemical synthesis and semisynthesis of proteins as they can be easily prepared using standard solid phase peptide synthesis (SPPS) and recombinant peptide techniques. Via treatment with NaNO2 and subsequent thiolysis, peptide hydrazides can be rapidly converted to peptide thioesters, which then selectively react with recombinant protein containing an N-terminal cysteine (Cys) to form a native peptide bond, thereby linking the two peptide segments without isolating any intermediates.

UI	MeSH Term	Description	Entries
D010455	Peptides	Members of the class of compounds composed of AMINO ACIDS joined together by peptide bonds between adjacent amino acids into linear, branched or cyclical structures. OLIGOPEPTIDES are composed of approximately 2-12 amino acids. Polypeptides are composed of approximately 13 or more amino acids. PROTEINS are considered to be larger versions of peptides that can form into complex structures such as ENZYMES and RECEPTORS.	Peptide,Polypeptide,Polypeptides
D011506	Proteins	Linear POLYPEPTIDES that are synthesized on RIBOSOMES and may be further modified, crosslinked, cleaved, or assembled into complex proteins with several subunits. The specific sequence of AMINO ACIDS determines the shape the polypeptide will take, during PROTEIN FOLDING, and the function of the protein.	Gene Products, Protein,Gene Proteins,Protein,Protein Gene Products,Proteins, Gene
D011994	Recombinant Proteins	Proteins prepared by recombinant DNA technology.	Biosynthetic Protein,Biosynthetic Proteins,DNA Recombinant Proteins,Recombinant Protein,Proteins, Biosynthetic,Proteins, Recombinant DNA,DNA Proteins, Recombinant,Protein, Biosynthetic,Protein, Recombinant,Proteins, DNA Recombinant,Proteins, Recombinant,Recombinant DNA Proteins,Recombinant Proteins, DNA
D002851	Chromatography, High Pressure Liquid	Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed.	Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D003545	Cysteine	A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.	Cysteine Hydrochloride,Half-Cystine,L-Cysteine,Zinc Cysteinate,Half Cystine,L Cysteine
D004952	Esters	Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water.	Ester
D006834	Hydrazines	Substituted derivatives of hydrazine (formula H2N-NH2).	Hydrazide
D006880	Hydroxy Acids	Organic compounds containing both the hydroxyl and carboxyl radicals.	Hydroxy Acid,Acid, Hydroxy,Acids, Hydroxy
D013438	Sulfhydryl Compounds	Compounds containing the -SH radical.	Mercaptan,Mercapto Compounds,Sulfhydryl Compound,Thiol,Thiols,Mercaptans,Compound, Sulfhydryl,Compounds, Mercapto,Compounds, Sulfhydryl
D060327	Solid-Phase Synthesis Techniques	Techniques used to synthesize chemicals using molecular substrates that are bound to a solid surface. Typically a series of reactions are conducted on the bound substrate that results in either the covalent attachment of specific moieties or the modification of existing function groups. These techniques offer an advantage to those involving solution reactions in that the substrate compound does not have to be isolated and purified between the reaction steps.	Solid-Phase Synthesis,Peptide Synthesis, Solid-Phase,Solid-Phase Nucleotide Synthesis,Solid-Phase Nucleotide Synthesis Techniques,Solid-Phase Peptide Synthesis,Solid-Phase Peptide Synthesis Techniques,Solid-Phase Synthesis Methods,Synthesis, Solid-Phase,Method, Solid-Phase Synthesis,Methods, Solid-Phase Synthesis,Nucleotide Syntheses, Solid-Phase,Nucleotide Synthesis, Solid-Phase,Peptide Syntheses, Solid-Phase,Peptide Synthesis, Solid Phase,Solid Phase Nucleotide Synthesis,Solid Phase Nucleotide Synthesis Techniques,Solid Phase Peptide Synthesis,Solid Phase Peptide Synthesis Techniques,Solid Phase Synthesis,Solid Phase Synthesis Methods,Solid Phase Synthesis Techniques,Solid-Phase Nucleotide Syntheses,Solid-Phase Peptide Syntheses,Solid-Phase Syntheses,Solid-Phase Synthesis Method,Solid-Phase Synthesis Technique,Syntheses, Solid-Phase,Syntheses, Solid-Phase Nucleotide,Syntheses, Solid-Phase Peptide,Synthesis Method, Solid-Phase,Synthesis Methods, Solid-Phase,Synthesis Technique, Solid-Phase,Synthesis Techniques, Solid-Phase,Synthesis, Solid Phase,Synthesis, Solid-Phase Nucleotide,Synthesis, Solid-Phase Peptide,Technique, Solid-Phase Synthesis,Techniques, Solid-Phase Synthesis