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N,N'-Diallyl-L-tartardiamide

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Chemical compound, polyacrylamide crosslinker
DATD
Skeletal formula of methylenebisacrylamide
Names
Preferred IUPAC name (2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-enyl)butanediamide
Identifiers
CAS Number
3D model (JSmol)
ECHA InfoCard 100.055.688 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16N2O4/c1-3-5-11-9(15)7(13)8(14)10(16)12-6-4-2/h3-4,7-8,13-14H,1-2,5-6H2,(H,11,15)(H,12,16)/t7-,8-/m1/s1Key: ZRKLEAHGBNDKHM-HTQZYQBOSA-N
SMILES
  • C=CCNC(=O)C(C(C(=O)NCC=C)O)O
Properties
Chemical formula C10H16N2O4
Molar mass 228.248 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

N,N′-Diallyl-L-tartardiamide (DATD) is a crosslinking agent for polyacrylamide gels, e.g., as used for SDS-PAGE. Compared to bisacrylamide gels, DATD gels have a stronger interaction with glass, and therefore are used in applications where the polyacrylamide gel acts as a "plug" structural component at the bottom of a gel electrophoresis apparatus, thereby preventing a weak discontinuous gel from sliding out from or otherwise moving within the apparatus. Unlike bisacrylamide-polyacrylamide gels, DATD-polyacrylamide gels can be conveniently dissolved using periodic acid due to the presence of viscinal diols in DATD. DATD is the slowest polyacrylamide crosslinker tested, and has can act as an inhibitor of polymerization at high concentrations.

See also

References

  1. ^ Baumann, Gerhard; Chrambach, Andreas (1976). "A highly crosslinked, transparent polyacrylamide gel with improved mechanical stability for use in isoelectric focusing and isotachophoresis". Analytical Biochemistry. 70 (1). Elsevier BV: 32–38. doi:10.1016/s0003-2697(76)80044-9. ISSN 0003-2697.
  2. Greaser, Marion L.; Warren, Chad M. (2018-11-14). "Electrophoretic Separation of Very Large Molecular Weight Proteins in SDS Agarose". Methods in Molecular Biology. New York, NY: Springer New York. pp. 203–210. doi:10.1007/978-1-4939-8793-1_18. ISBN 978-1-4939-8792-4. ISSN 1064-3745.
  3. Tas, Johan; de Vries, Alfons C.J.; Berndsen, RenéG. (1979). "A method for the quantitative determination of protein incorporated in solubilizable polyacrylamide gels". Analytical Biochemistry. 100 (2). Elsevier BV: 264–270. doi:10.1016/0003-2697(79)90229-x. ISSN 0003-2697.
  4. ^ Gelfi, Cecilia; Righetti, Pier Giorgio (1981). "Polymerization kinetics of polyacrylamide gels I. Effect of different cross-linkers". Electrophoresis. 2 (4). Wiley: 213–219. doi:10.1002/elps.1150020404. ISSN 0173-0835.
  5. Hahn, Edwin C.; Hahn, Patricia S. (1987). "Properties of acrylamide gels cross-linked with low concentrations of N,N′-diallyltartardiamide". Journal of Virological Methods. 15 (1). Elsevier BV: 41–52. doi:10.1016/0166-0934(87)90047-4. ISSN 0166-0934.
  6. Neumann, Ulf; Khalaf, Hosni; Rimpler, Manfred (1992). "Quantitation of proteins separated in N,N′-1,2-dihydroxyethylenebisacrylamide-crosslinkedpolyacrylamide gels". Analytical Biochemistry. 206 (1). Elsevier BV: 1–5. doi:10.1016/s0003-2697(05)80002-8. ISSN 0003-2697.


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