DL-Arabinose → Pentosidine

HRID 249395

Reaction equation

HRID 249395 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 co-eluting 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-bffb7174a0ac4af9a4dc20f013edb573
Source dataset
uspto-grants-1993_05
Patent number
US05214138

Linked notes

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