DEPBT | CAS#165534-43-0 | coupling reagent

MedKoo Cat#: 145403 | Name: DEPBT

Description:

WARNING: This product is for research use only, not for human or veterinary use.

DEPBT is an effective coupling reagent for synthesis of linear and cyclic peptides by both solution and solid-phase peptide synthesis. DEPBT mediates amide bond formation with remarkable resistance to racemization. DEPBT results in a higher cyclization yield compared with other coupling reagents. DEPBT mediates amide bond formation with a remarkable resistance to racemization.

Chemical Structure

DEPBT

CAS#165534-43-0

Theoretical Analysis

MedKoo Cat#: 145403

Name: DEPBT

CAS#: 165534-43-0

Chemical Formula: C11H14N3O5P

Exact Mass: 299.0671

Molecular Weight: 299.22

Elemental Analysis: C, 44.15; H, 4.72; N, 14.04; O, 26.73; P, 10.35

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

DEPBT;

IUPAC/Chemical Name

diethyl (4-oxobenzo[d][1,2,3]triazin-3(4H)-yl) phosphate

InChi Key

AJDPNPAGZMZOMN-UHFFFAOYSA-N

InChi Code

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

SMILES Code

CCOP(=O)(OCC)ON1N=NC2=CC=CC=C2C1=O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 299.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Ye YH, Li H, Jiang X. DEPBT as an efficient coupling reagent for amide bond formation with remarkable resistance to racemization. Biopolymers. 2005;80(2-3):172-8. doi: 10.1002/bip.20201. PMID: 15627282. 2: Tang YC, Xie HB, Tian GL, Ye YH. Synthesis of cyclopentapeptides and cycloheptapeptides by DEPBT and the influence of some factors on cyclization. J Pept Res. 2002 Aug;60(2):95-103. doi: 10.1034/j.1399-3011.2002.201000.x. PMID: 12102722. 3: Keppler BK, Berger MR, Heim ME. New tumor-inhibiting metal complexes. Cancer Treat Rev. 1990 Sep;17(2-3):261-77. doi: 10.1016/0305-7372(90)90057-m. PMID: 2272042. 4: Li H, Jiang X, Ye YH, Fan C, Romoff T, Goodman M. 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization. Org Lett. 1999 Jul 15;1(1):91-3. doi: 10.1021/ol990573k. PMID: 10822541. 5: Goodman M, Zapf C, Rew Y. New reagents, reactions, and peptidomimetics for drug design. Biopolymers. 2001;60(3):229-45. doi: 10.1002/1097-0282(2001)60:3<229::AID-BIP10034>3.0.CO;2-P. PMID: 11774229. 6: Lam PL, Wu Y, Wong KL. Incorporation of Fmoc-Dab(Mtt)-OH during solid-phase peptide synthesis: a word of caution. Org Biomol Chem. 2022 Mar 30;20(13):2601-2604. doi: 10.1039/d2ob00070a. Erratum in: Org Biomol Chem. 2022 Mar 30;20(13):2729. doi: 10.1039/d2ob90038f. PMID: 35258068. 7: Ait-Mohand S, Fournier P, Dumulon-Perreault V, Kiefer GE, Jurek P, Ferreira CL, Bénard F, Guérin B. Evaluation of 64Cu-labeled bifunctional chelate-bombesin conjugates. Bioconjug Chem. 2011 Aug 17;22(8):1729-35. doi: 10.1021/bc2002665. Epub 2011 Jul 29. PMID: 21761921. 8: Caruso F, Rossi M. Antitumor titanium compounds. Mini Rev Med Chem. 2004 Jan;4(1):49-60. doi: 10.2174/1389557043487565. PMID: 14754443. 9: Liu M, Tang YC, Fan KQ, Jiang X, Lai LH, Ye YH. Cyclization of several linear penta- and heptapeptides with different metal ions studied by CD spectroscopy. J Pept Res. 2005 Jan;65(1):55-64. doi: 10.1111/j.1399-3011.2004.00199.x. PMID: 15686535. 10: Jeremic T, Linden A, Heimgartner H. New 21- and 24-atom Aib-containing cyclopeptides. J Pept Sci. 2008 Sep;14(9):1051-61. doi: 10.1002/psc.1041. PMID: 18523966. 11: Yan C, Qi F, Li S, Xu J, Liu C, Meng Z, Qiu L, Xue M, Lu W, Yan Z. Functionalized photonic crystal for the sensing of Sarin agents. Talanta. 2016 Oct 1;159:412-417. doi: 10.1016/j.talanta.2016.06.045. Epub 2016 Jun 21. PMID: 27474325. 12: Kirichenko K, Hillman JD, Handfield M, Park JH. Complete synthesis of the bicyclic ring of a mutacin analog with orthogonally protected lanthionine via solid-phase intracyclization. J Pept Sci. 2019 Nov;25(11):e3214. doi: 10.1002/psc.3214. PMID: 31721375. 13: Goodman M, Cai W, Smith ND. The bold legacy of Emil Fischer. J Pept Sci. 2003 Sep;9(9):594-603. doi: 10.1002/psc.476. PMID: 14552421. 14: Kula M, Jiang J, Lu W, Luo Y. Effects of hydrogen bonding on current-voltage characteristics of molecular junctions. J Chem Phys. 2006 Nov 21;125(19):194703. doi: 10.1063/1.2364494. PMID: 17129146. 15: Cai W, Wong D, Kinberger GA, Kwok SW, Taulane JP, Goodman M. Facile and efficient assembly of collagen-like triple helices on a TRIS scaffold. Bioorg Chem. 2007 Aug;35(4):327-37. doi: 10.1016/j.bioorg.2007.01.003. Epub 2007 Mar 21. PMID: 17368718. 16: Caruso F, Rossi M. Antitumor titanium compounds and related metallocenes. Met Ions Biol Syst. 2004;42:353-84. PMID: 15206108. 17: Schilling T, Keppler KB, Heim ME, Niebch G, Dietzfelbinger H, Rastetter J, Hanauske AR. Clinical phase I and pharmacokinetic trial of the new titanium complex budotitane. Invest New Drugs. 1996;13(4):327-32. doi: 10.1007/BF00873139. PMID: 8824351. 18: Pereira ML, Garcia e Costa F. The blood-testis barrier as a target of some chemotherapeutic agents. Chemotherapy. 2007;53(6):446-8. doi: 10.1159/000110017. Epub 2007 Oct 23. PMID: 17957098. 19: Woo GH, Beeler AB, Snyder JK. 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron. 2007 Jun 18;63(25):5649-5655. doi: 10.1016/j.tet.2007.04.003. PMID: 19112520; PMCID: PMC2608727. 20: Dubler E, Buschmann R, Schmalle HW. Isomer abundance of bis(beta-diketonato) complexes of titanium(IV). Crystal structures of the antitumor compound budotitane [Ti(IV)(bzac)(2)(OEt)(2)] and of its dichloro-derivative [Ti(IV)(bzac)(2)Cl(2)] (bzac=1-phenylbutane-1,3-dionate). J Inorg Biochem. 2003 Jun 1;95(2-3):97-104. doi: 10.1016/s0162-0134(03)00091-6. PMID: 12763653.