DEPBT (3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one) is a

peptide Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides that have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty am ...

coupling reagent used in

peptide synthesis In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl ...

. It shows remarkable resistance to

racemization In chemistry, racemization is a conversion, by heat or by chemical reaction, of an optically active compound into a racemic (optically inactive) form. This creates a 1:1 molar ratio of enantiomers and is referred to as a racemic mixture (i.e. cont ...

. Fmoc-Dab(Mtt)-OH, a commercially available amino acid building block for solid-phase peptide synthesis (SPPS), was proven to undergo rapid lactamization, instead of reacting with the

N-terminal end The N-terminus (also known as the amino-terminus, NH2-terminus, N-terminal end or amine-terminus) is the start of a protein or polypeptide, referring to the free amine group (-NH2) located at the end of a polypeptide. Within a peptide, the amin ...

of the

. Compared with other commercially available coupling reagents, DEPBT has shown superior performance in coupling Fmoc-Dab(Mtt)-OH to the

during SPPS, though the approach was regarded as 'costly and tedious'.

References

Peptide coupling reagents Biochemistry Biochemistry methods Reagents for biochemistry Organophosphates Benzotriazines Ethyl esters {{alkanederivative-stub

See also

References