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DTBP (Dimethyl 3,3Ā“-dithiobispropionimidateā€¢2 HCl)


A cleavable, bifunctional, imidoester crosslinker.

Pierce DTBP

Thermo Scientific Pierce DTBP is dimethyl 3,3'-dithiobispropionimidate, a crosslinker that contains amine-reactive imidoester groups around an 8-atom spacer arm, whose central disulfide bond can be cleaved with reducing agents.

Dimethyl dithiobispropionimidate (DTBP) is a homobifunctional, cleavable and membrane permeable crosslinker. It contains an amine-reactive imidoester at each end of an 8-atom spacer arm. Imidoesters react with primary amines at pH 8-10 to form stable amidine bonds. The amidine is protonated and therefore, like the lysine it modified, has a positive charge at physiological pH. Proteins, including antibodies, generally have several primary amines in the side chain of lysine (K) residues and the N-terminus of each polypeptide that are available as targets for imidoester crosslinking reagents.

Highlights:

  • Reactive groups: imidoester (both ends)
  • Reactive towards: amino groups (primary amines)
  • Imidoester reacts rapidly with any primary amine-containing molecule to form amidine bonds
  • Cleavable by reduction of spacer arm disulfide bond with DTT, TCEP or other reducing agents
  • Compare to DMS (non-cleavable)
  • Water-soluble

Applications:

  • Reversibly crosslink and stabilize protein-protein interactions
  • Stabilize protein interactions prior to ChIP assays to capture indirect protein interactions

Product Details:

Dimethyl 3,3'-dithiobispropionimidate-2HCl; DTBP
 
Chemical structure of DST crosslinking reagent.

DTBP crosslinks can be easily reversed by the addition of 100-150 mM DTT at 37°C for 30 minutes. DMS, the non-cleavable analog of DTBP is available for applications that require a stable, non-cleavable bond. DTSSP, the NHS-ester analog of DTBP is also available for applications that require crosslinking at physiologic pH or greater stability of the crosslinked product at elevated pH. DTBP and DMS have essentially identical crosslinking activity toward primary amines.

Properties of DTBP.
Alternative names Cleavable DMS
Molecular formula C8H18N2O2S2Cl2
Molecular weight 309.28
Spacer arm length 11.9 Å (8 atoms)
CAS number 38285-78-8
Storage conditions 4°C, protect from moisture, use only fresh solutions
Reactive groups Imidoesters, react with primary amines at pH 8-10

DTBP Specifications:

We manufacture DTBP to the highest specifications to produce the most specific bioconjugates, ensure the integrity of your data and to provide you with the highest degree of consistency. Each lot of DTBP cross-linker is tested to meet the following minimum specifications.

  • Identity: IR scan shows only peaks characteristic of the structure and functional groups of DTBP
  • Melting point: begins melting between 170-178°C, melts within a 2°C range

References:

  1. Mattson, G., et al. (1993). A practical approach to cross-linking. Molecular Biology Reports 17, 167-183.
  2. Hand, E.S., and Jencks, W.P. (1962). Mechanism of the reaction of imidoesters with amines. J. Am. Chem. Soc . 84, 3505-3514.
  3. Packman, L.C. and Perhan, R.N. (1982). Quaternary Structures the Pyruvate Dehydrogenase Multienzyme Complex of Bacillus Stearothermophilus Studies by a New Reversible Crosslinking Procedure with Bis(imidoesters). Biochem . 21, 5171-5175.
  4. Shivdasani, R.A. and Thomas, D.W. (1988). Molecular associations of IA antigens after T-B cell interactions. J. Immunol. 141, 1252-1260.
  5. Jerng, H.H., Kunjilwar, K. and Pfaffinger, P.J. (2005). Multiprotein assembly of Kv4.2, KChIP3 and DPP10 produces ternary channel complexes with I SA-like properties. J. Physiol. 568, 767-788.

Product References:

Crosslinker Application Guide -- search for recent literature references for this product

Related Resources:

Overview of crosslinking
Chemistry of crosslinking

Related Products:

Crosslinkers at a glance (selection guide)
DMS (non-cleavable equivalent)
DTSSP (sulfo-NHS ester equivalent)
Bioconjugate Techniques (book)


Ordering Information
 
Product # Description Pkg. Size Instructions MSDS CofA Price
20665 DTBP (Wang and Richard's Reagent)
Formulation: Dimethyl 3,3'-dithiobispropionimidate-2HCl; crystalline powder solid
Sufficient For: 3233mL of typical 1X (1mM) reaction solution, or approx. 500 uses at 2mg reagent per use
1g Product Instructions for product #20665 DTBP (Wang and Richard's Reagent) MSDS for product #20665 DTBP (Wang and Richard's Reagent) Certificate of Analysis for product #20665 DTBP (Wang and Richard's Reagent) $169.00

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Instructions | MSDS | CofA
Product Instructions | MSDS | CofA  

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