(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 1826567Notes

Reaction equation

[OH:1][CH2:2][C:3]([C@H:5]([C@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].[OH:13][CH:14]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:19]([O:20][C@@H:21]2[O:29][C@H:28]([CH2:30][OH:31])[C@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]2[OH:23])[C@H:17]([OH:18])[C@H:15]1[OH:16]>>[OH:13][CH:14]1[O:33][C@H:32]([CH2:34][OH:35])[C@@H:19]([O:20][C@@H:21]2[O:29][C@H:28]([CH2:30][OH:31])[C@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]2[OH:23])[C@H:17]([OH:18])[C@H:15]1[OH:16].[O:1]=[CH:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])[OH:4]

Participants

Reactant 2

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

HCID 440995(+)-Lactose

Product 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HCID 440995(+)-Lactose

Procedure

U.S. Pat. No. 6,057,135 discloses a process for manufacturing D-tagatose, wherein a lactose permeate is hydrolysed to obtain a lactose hydrolysate comprising D-galactose and glucose. The hydrolysate is fermented to convert the glucose to ethanol which is subsequently removed and the remaining solution of D-galactose is subjected to enzymatic isomerisation with an L-arabinose isomerase to obtain D-tagatose. The L-arabinose isomerase preparations used are crude biomass extracts of Lactobacillus pentosus, Bacillus amyloliquefaciens or Arthrobacter spp

Sources & evidence

ORD record: ord-154739cbc3434d108778b3365d111749
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07052898B2

Reaction notes

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