DL-Arabinose → Pentosidine

HRID 374409Notes

Reaction equation

HRID 374409 reaction equation
[CH2:1](O)[CH:2](O)[CH:3](O)[CH:4](O)[CH:5]=O.[NH2:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].[NH2:21][C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:29])[NH2:28].O=C[C@@H]([C@@H]([C@@H](CO)O)O)O>>[CH:2]1[CH:3]=[C:4]2[C:5](=[N:29][C:27]([NH:26][CH2:25][CH2:24][CH2:23][C@H:22]([NH2:21])[C:30]([OH:32])=[O:31])=[N:28]2)[N:17]([CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]([NH2:11])[C:18]([OH:20])=[O:19])[CH:1]=1

Participants

5

Reactant 4

HCID 854DL-ArabinoseHCID 5962L-LysineHCID 5311110Aldehydo-D-riboseHCID 178418600HCID 178418600, compound

Product 1

HCID 119593Pentosidine

Conditions

Temperature
80 °C

Procedure

In order to confirm the pentose-derived nature of the native fluorophore 100 mM each of L-lysine, L-arginine and D-ribose were heated for 1 hour at 80° C. Injection of a small amount of this synthetic material on HPLC revealed a major fluorescent peak coeluting with the native fluorophore. (see FIG. 5) In order to substantiate the proposed structure, the synthetic fluorophore was prepared preparatively and purified. Total yield was 21 mg; i.e., 0.02% of the reactants.

Workup

  1. customthe synthetic fluorophore was prepared preparatively
  2. custompurified

Sources & evidence

ORD record
ord-8357ab42bf30496287c2be5cf03b34d8
Source dataset
uspto-grants-1996_01
Patent number
US05480807

Reaction notes

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