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N,N'-Diallyl-L-tartardiamide

N,N′-Diallyl-L-tartardiamide (DATD) is a crosslinking agent for polyacrylamide gels, e.g., as used for SDS-PAGE.[1] 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.[1][2] Unlike bisacrylamide-polyacrylamide gels, DATD-polyacrylamide gels can be conveniently dissolved using periodic acid due to the presence of viscinal diols in DATD.[3] DATD is the slowest polyacrylamide crosslinker tested,[4] and has can act as an inhibitor of polymerization at high concentrations.[4][5][6]

DATD
Skeletal formula of methylenebisacrylamide
Names
Preferred IUPAC name
(2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-enyl)butanediamide
Identifiers
3D model (JSmol)
ECHA InfoCard 100.055.688 Edit this at Wikidata
  • 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/s1
    Key: ZRKLEAHGBNDKHM-HTQZYQBOSA-N
  • C=CCNC(=O)C(C(C(=O)NCC=C)O)O
Properties
C10H16N2O4
Molar mass 228.248 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

See also

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References

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  1. ^ a b 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. ^ a b 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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