DEPBT (3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one) is a
peptide
Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides.
A ...
coupling reagent used in
peptide synthesis. It shows remarkable resistance to
racemization.
Fmoc-Dab(Mtt)-OH, a commercially available amino acid building block for
solid-phase peptide synthesis (SPPS), was proven to undergo rapid
lactamization
A lactam is a cyclic amide, formally derived from an amino alkanoic acid. The term is a portmanteau of the words ''lactone'' + ''amide''.
Nomenclature
Greek prefixes in alphabetical order indicate ring size:
* α-Lactam (3-atom rings)
* β-Lacta ...
, 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
peptide
Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides.
A ...
. Compared with other commercially available
coupling reagents, DEPBT has shown superior performance in coupling Fmoc-Dab(Mtt)-OH to 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
peptide
Peptides (, ) are short chains of amino acids linked by peptide bonds. Long chains of amino acids are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides.
A ...
during
SPPS, though the approach was regarded as 'costly and tedious'.
See also
*
BOP
*
PyBOP
PyBOP (benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate) is a peptide coupling reagent used in solid phase peptide synthesis. It is used as a substitute for the BOP reagent - avoiding the formation of the carcinogenic waste product ...
References
Peptide coupling reagents
Biochemistry
Biochemistry methods
Reagents for biochemistry
Organophosphates
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