D-Arabinose → 6-deoxy-L-sorbose

HRID 1941738Notes

Reaction equation

O=C[C@H]([C@@H]([C@@H](CO)O)O)O.[O:11]=[CH:12][C@H:13]([C@@H:15]([C@@H:17]([C@H:19]([CH3:21])[OH:20])[OH:18])[OH:16])[OH:14].OCC([C@@H]([C@@H]([C@H](C)O)O)O)=O.OCC([C@H]([C@H]([C@@H](CO)O)O)O)=O>>[OH:11][CH2:12][C:13]([C@H:15]([C@@H:17]([C@H:19]([CH3:21])[OH:20])[OH:18])[OH:16])=[O:14]

Participants

Reactant 4

HCID 66308D-Arabinose

HCID 92092(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

HCID 3034656L-(-)-Fucose

HCID 6857362L-Fuculose

Product 1

HCID 4393306-deoxy-L-sorbose

Procedure

With D-arabinose isomerase, L-fucose (6-deoxy L-galactose) was isomerized to 6-deoxy L-tagatose, which was further epimerized with D-tagatose 3-epimerase, to produce 6-deoxy L-sorbose.

Sources & evidence

ORD record: ord-b8d61152588a4bdda47de79ca5c6fd32
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389248B2

Reaction notes

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