Synthetic peptide coupling requires the ..

A practical example of EDC's utility is the solution synthesis of human epidermal growth factor, a 53-residue protein. This included several couplings of fragments ranging from three to six residues in length.

Peptide coupling reagents are used ..

N,N'-dicyclohexylcarbodiimide (DCC) is one of the most common peptide coupling agents.

Solid-Phase Peptide Synthesis - Furman Student …

The procedure can result in extensive racemization of both reactants and products which may be supressed by the addition of HOSu; presumably an HOSu ester is the penultimate intermediate. The addition of HOSu also decreases racemization in polypeptide synthesis when {[(MeN)P+]O (BF-)} is used as the coupling agent.A rather unusual coupling reaction between HOSu and glyoxylic acid tosylhydrazone leads to succinimidyl diazoacetate (eq 4); again, the leaving ability of the HOSu residue renders this a useful compound for effecting the direct transfer of a diazoacetyl function to amines, phenols, and peptides.Modified Barton-McCombie intermediates are best prepared from pentafluorophenyl chlorothionoformate and a catalytic quantity (15-20%) of HOSu in refluxing benzene rather than by using , the rather more conventional catalyst of acyl group transfer (eq 5).

Solid-phase peptide synthesis was invented by Merrifield

The low solubility of DCU in most organic solvents complicates purifications, especially in the peptide synthesis.DCC can be prepared from DCU by treatment with ­phosphorus pentoxide [] (Scheme 1).


Coupling Reagents in Peptide Synthesis ..

A typical example of EDC for peptide coupling is shown in (eq 1).The problems associated with carbodiimide couplings are mainly from the -acylisourea intermediate (1) having poor selectivity for specific nucleophiles.

This was a rev= olution in polypeptide synthesis, ..

Jeon and co-workers published the solid-phase ­synthesis of 2-amino-2-thiazolines using the DCC-mediated ­cyclization of N-(2-hydroxyethyl)thioureas.14

“Recent development of peptide coupling reagents ..

DCC (acronym for N,N'-dicyclohexylcarbodiimide) is an organic compound with chemical formula C13H22N2 whose primary use is to couple amino acids during artificial protein synthesis. Under standard conditions, DCC exists in the form of white crystals with a heavy, sweet odor. The low melting point of this material allows it to be melted for easy handling. DCC is highly soluble in dichloromethane, tetrahydrofuran, acetonitrile and dimethylformamide, but insoluble in water.

BOP reagent|Peptide coupling reagent|CAS# 56602-33-6

Of the several syntheses of DCC, Pri-Bara et. al. use palladium acetate, iodine, and oxygen to couple cyclohexyl amine and cyclohexyl isocyanide. Yields of up to 67% have been achieved using this reaction scheme. The reaction is as follows:

In peptide synthesis using HBTU/HOBt coupling, Why is …

Lemaire and co-workers used DCC in the synthesis of alkaloid (+)-isoretronecanol.1 DCC was also used in polypeptide synthesis.2 (B) Synthesis of esters, lactones, and thioesters: In some cases it is necessary to carry out the esterification in two steps.

resin with an Fmoc-Amino acid for solid-phase peptide synthesis

thorough study of the mechanism in each method involving basic producer for logistic and technical support is a necessary term for the optimization of the coupling step of a new peptide drug and further up-scaling towards bulk manufacturing.

Mechanism of DCC-promoted peptide coupling.

The disubstituted carboxyl activating agents are used for crosslinking proteins to nucleic acids and formation of immunoconjugates in peptide synthesis.