Citrulline → N-(2,3,4,5-tetrahydroxy-pentyl)-L-(+)-citrulline

HRID 438013

Reaction equation

HRID 438013 reaction equation
O=[CH:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[NH2:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[O:18]>[Ni]>[OH:4][CH:3]([CH:5]([OH:6])[CH:7]([OH:8])[CH2:9][OH:10])[CH2:2][NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[O:18]

Participants

4

Reactant 2

HCID 9750CitrullineHCID 5311110Aldehydo-D-ribose

Product 1

HCID 54340382N-(2,3,4,5-tetrahydroxy-pentyl)-L-(+)-citrulline

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

The product was made from D-ribose and L-(+)-citrulline using Raney nickel as a catalyst and heating for 2 hours to 50° C. and for 4 hours to 70° C. The product obtained had a melting point of 172° to 175° C. (decomposition) and an RF -value of 0.52 (determined as indicated under Example T).

Workup

  1. temperatureheating for 2 hours to 50° C. and for 4 hours to 70° C
  2. customThe product obtained

Sources & evidence

ORD record
ord-83b4416ca09743c682d22a1ff915884c
Source dataset
uspto-grants-1977_06
Patent number
US04032676

Linked notes

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