L-Lysine → Pentosidine

HRID 374408

Reaktionsgleichung

Reaktionsgleichung von HRID 374408
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[NH2:13][C@H:14]([C:20]([OH:22])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19].O=[CH:24][C@@H:25]([C@@H:27]([C@@H:29]([CH2:31]O)O)O)O>>[CH:25]1[CH:27]=[C:29]2[C:31](=[N:9][C:7]([NH:6][CH2:5][CH2:4][CH2:3][C@H:2]([NH2:1])[C:10]([OH:12])=[O:11])=[N:8]2)[N:19]([CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]([NH2:13])[C:20]([OH:22])=[O:21])[CH:24]=1

Komponenten

4

Edukt 3

HCID 5962L-LysineHCID 5311110Aldehydo-D-riboseHCID 178418600HCID 178418600, Verbindung

Produkt 1

HCID 119593Pentosidine

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Three liters containing 100 mM each of L-arginine, L-lysine and D-ribose, at pH 7.3, were heated for 1 hr at 80° C. The cooled mixture was poured onto a Buchner funnel filled with Dowex 50×4-400 ion-exchange resin (Aldrich Chem. Co., Inc., Milwaukee, Wisc.) equilibrated according to conditions of Boas (Boas, N. F., J. Biol. Chem., 204, pp. 553-563, 1953). The resin was washed with 2 liters each of water and 1 M pyridine, followed by elution of pentosidine-containing material with 1 liter of 2 N NaOH. The material was then adjusted to pH 7.4 with HCl, concentrated by rotary evaporation, passed through a Bio-Gel P-2 column and purified by HPLC as described above. The material was also chromatographed on Whatman 17 Chr paper (Whatman Inc., Clifton, N.J.) using 1:1 water/pyridine. Upon elution from the paper, the material was reinjected and collected by reversed-phase HPLC using TFA as the counterion.

Aufarbeitung

  1. additionThe cooled mixture was poured onto a Buchner funnel
  2. additionfilled with Dowex 50×4-400 ion-exchange resin (Aldrich Chem. Co., Inc., Milwaukee, Wisc.)
  3. washThe resin was washed with 2 liters each of water and 1 M pyridine
  4. washfollowed by elution of pentosidine-
  5. additioncontaining material with 1 liter of 2 N NaOH
  6. concentrationconcentrated by rotary evaporation
  7. custompurified by HPLC
  8. customThe material was also chromatographed on Whatman 17 Chr paper (Whatman Inc., Clifton, N.J.)
  9. washUpon elution from the paper
  10. customcollected by reversed-phase

Quellen und Nachweise

ORD-Eintrag
ord-77b72368205b40a28b4158678546eddf
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05480807

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