N , N ′ -diallyl tartaric acid diamide

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Structural formula
N, N′-diallyl-L-tartaric acid diamide
General
Surname N , N ′ -diallyl- L -tartaric acid diamide
other names
  • (+) - N , N ' -diallyl- L -tartaric acid diamide
  • DATD
Molecular formula C 10 H 16 N 2 O 4
Brief description

white solid

External identifiers / databases
CAS number 58477-85-3
EC number 261-277-3
ECHA InfoCard 100,055,688
PubChem 94074
ChemSpider 88941
Wikidata Q55524605
properties
Molar mass 228.25 g mol −1
Physical state

firmly

Melting point

184-186 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-280-305 + 351 + 338-304 + 340-405-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N , N ′ -Diallyl tartaric acid diamide (DATD) is a chemical compound from the group of tartaric acids . If in this article or in the scientific literature " N , N ' is mentioned -Diallylweinsäurediamid" always is almost N , N -Diallyl-' L -weinsäurediamid meant a derivative of the natural L -tartaric acid.

properties

N , N ′ -diallyl- L -tartaric acid diamide is a solid. It is used in biochemistry as a crosslinker in polyacrylamide gel electrophoresis instead of N , N ′ -methylene bisacrylamide (Bis). As a result, after the electrophoretic separation, the gel can be dissolved by glycol cleavage using a variant of gel extraction with a sodium periodate solution . Therefore the gels are also referred to as reversible gels. However, N , N ′ -diallyl- L- tartaric acid diamide also inhibits the polymerization in the polyacrylamide gel , which means that more neurotoxic monomers occur in the finished gel. The resulting gels are very transparent and elastic. They also adhere more strongly to the glass plates after the gel has polymerized. Of eight possible crosslinkers for polyacrylamide gels, DATD reacts slowest with proteins .

Alternatively, ethylene diacrylate can sometimes be used as a cleavable crosslinker in polyacrylamide gels.

Various derivatives of N , N '-diallyl- L -tartaric acid diamide are used for the modification of stationary phases in chromatography columns in HPLC .

history

N , N '-Diallyl- L -tartaric acid diamide was first used in 1970 as a crosslinker for polyacrylamide gel electrophoresis with the purpose of cleavage.

literature

  • PJ Späth, H. Koblet: Properties of SDS-polyacrylamide gels highly cross-linked with N, N'-diallyltartardiamide and the rapid isolation of macromolecules from the gel matrix. In: Analytical Biochemistry . Volume 93, Number 2, March 1979, pp. 275-285, PMID 464262 .

Individual evidence

  1. ↑ Data sheet (+) - N, N′-diallyltartramide ≥99% from Sigma-Aldrich , accessed on February 14, 2018 ( PDF ).
  2. ↑ a b c d e data sheet N, N′-Diallyl-L-tartardiamide, 99% from AlfaAesar, accessed on February 13, 2018 ( PDF )(JavaScript required) .
  3. ↑ Nicholas Catsimpoolas: Methods of Protein Separation. Springer Science & Business Media, 2013, ISBN 978-1-468-49984-1 , p. 322.
  4. ↑ RS Kelkar, A. Mahen, AM Saoji, SS Kelkar: NN 'diallyltartardiamide (DATD) as a cross-linking agent for polyacrylamide gel disc electrophoresis of human serum proteins. In: Journal of Postgraduate Medicine . Volume 32, Number 1, January 1986, pp. 27-31, PMID 3746707 .
  5. ↑ BD Hames: Gel Electrophoresis of Proteins. OUP Oxford, 1998, ISBN 978-0-191-56563-2 , p. 136.
  6. ↑ a b G. Baumann, A. Chrambach: A highly crosslinked, transparent polyacrylamide gel with improved mechanical stability for use in isoelectric focusing and isotachophoresis. In: Analytical Biochemistry . Volume 70, Number 1, January 1976, pp. 32-38, PMID 1259153 .
  7. ↑ M. Galvani, M. Hamdan, PG Righetti: Investigating the reaction of a number of gel electrophoresis cross-linkers with beta-lactoglobulin by matrix assisted laser desorption / ionization-mass spectrometry. In: Electrophoresis . Volume 21, Number 17, November 2000, pp. 3684-3692, doi : 10.1002 / 1522-2683 (200011) 21:17 <3684 :: AID-ELPS3684> 3.0.CO; 2-E , PMID 11271487 .
  8. ↑ GL Choules, BH Zimm: An acrylamide gel soluble in scintillation fluids: its application to electrophoresis at neutral and low pH. In: Analytical Biochemistry . Volume 13, Number 2, November 1965, pp. 336-344, PMID 5863690 .
  9. ^ Charles W. Gehrke: Chromatography-A Century of Discovery 1900-2000 The Bridge to The Sciences / Technology. Elsevier, 2001, ISBN 978-0-080-47650-6 , p. 120.
  10. ↑ HS Anker: A solubilizable acrylamide gel for electrophoresis. In: FEBS Letters . Volume 7, Number 3, April 1970, p. 293, PMID 11947496 .