N,N'-Diallyl-L-tartardiamide

DATD
Names
	Preferred IUPAC name (2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-enyl)butanediamide
Identifiers
CAS Number	58477-85-3 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.055.688
PubChem CID	94074;
CompTox Dashboard (EPA)	DTXSID60886266 ;
	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/s1 Key: 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−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

References

^ ^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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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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[Baumann1976-1] 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.

[Greaser2018-2] 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.

[Tas_de_Vries_Berndsen_1979_pp._264–270-3] 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.

[Gelfi-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.

[Hahn_Hahn_1987_pp._41–52-5] 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.

[Neumann_Khalaf_Rimpler_1992_pp._1–5-6] 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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See also

References