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]

Quick facts Names, Identifiers ...

DATD

Names
Preferred IUPAC name (2R,3R)-2,3-dihydroxy-N,N'-bis(prop-2-enyl)butanediamide
Identifiers
CAS Number	58477-85-3 Y
3D model (JSmol)	Interactive image
ChemSpider	88941
ECHA InfoCard	100.055.688
EC Number	261-277-3
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

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