DEPBT

DEPBT (3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one) is a peptide coupling reagent used in peptide synthesis. It shows remarkable resistance to racemi…

DEPBT
DEPBT
Names
Preferred IUPAC name
Diethyl 4-oxo-1,2,3-benzotriazin-3(4H)-yl phosphate
Other names
DEPBT
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.337 Edit this at Wikidata
UNII
  • InChI=1S/C11H14N3O5P/c1-3-17-20(16,18-4-2)19-14-11(15)9-7-5-6-8-10(9)12-13-14/h5-8H,3-4H2,1-2H3
    Key: AJDPNPAGZMZOMN-UHFFFAOYSA-N
  • CCOP(=O)(OCC)On1c(=O)c2ccccc2nn1
Properties
C11H14N3O5P
Molar mass 299.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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DEPBT (3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one) is a peptide coupling reagent used in peptide synthesis. It shows remarkable resistance to racemization.[1]

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 of the peptide. Compared with other commercially available coupling reagents, DEPBT has shown superior performance in coupling Fmoc-Dab(Mtt)-OH to the N-terminal end of peptide during SPPS, though the approach was regarded as 'costly and tedious'.[2]

See also

References

  1. ^ Li, Haitao; Jiang, Xiaohui; Ye, Yun-hua; Fan, Chongxu; Romoff, Todd; Goodman, Murray (1999). "3-(Diethoxyphosphoryloxy)-1,2,3- benzotriazin-4(3H)-one (DEPBT): A New Coupling Reagent with Remarkable Resistance to Racemization". Organic Letters. 1 (1): 91–94. doi:10.1021/ol990573k. ISSN 1523-7060. PMID 10822541.
  2. ^ Lam, Pak-Lun; Wu, Yue; Wong, Ka-Leung (2022). "Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution". Organic & Biomolecular Chemistry. 20 (13): 2601–2604. doi:10.1039/D2OB00070A. PMID 35258068.


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