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Sorbitol → Glucamine

HRID 1389858
Notes
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Reaction equation

HRID 1389858 reaction equation
OC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[NH2:13][CH2:14][C@H:15]([OH:24])[C@@H:16]([OH:23])[C@H:17]([OH:22])[C:18](=[O:21])[CH2:19][OH:20]>>[NH2:13][CH2:14][C@@H:15]([C@H:16]([C@@H:17]([C@@H:18]([CH2:19][OH:20])[OH:21])[OH:22])[OH:23])[OH:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 5780SorbitolHCID 86737446(3S,4R,5S)-6-amino-1,3,4,5-tetrahydroxyhexan-2-one

Product 1

HCID 452501Glucamine

Procedure

Glucobacter oxydans ssp. suboxydans is cultured, on a 10 l scale, in a fermenter in a medium which contains, per 1 l, 100 g of sorbitol, 20 g of yeast extract and 2 g of KH2PO4 --dissolved in tap water. 5 l of air per minute are blown through the fermenter and the fermenter is stirred at 500 rpm and kept at a temperature of 30° C. After a 16 hour incubation period, the cells are centrifuged off from the culture broth, washed once by suspending in 10 mM KH2PO4 and again centrifuging and then suspended in 300 ml of 10 mM KH2PO4. The cell suspension thus obtained is broken up by passing twice through a French pressure cell under 8 bars. The cell-free extract is introduced into a 1 l conical flask, 1-amino-1-deoxy-D-glucitol (oxalate salt) is added to give a concentration of 10 g/l and the mixture is incubated at 30° C. on a rotary shaker at 280 rpm. After 7 hours it is possible to detect 3.7 g/l of 6-amino-6-deoxy-L-sorbose--corresponding to a 37% conversion--in this extract, with the aid of the saccharase inhibitory activity. The reaction is discontinued at this time and the extract is worked up as indicated in Example 1.

Workup

  1. extractionextract
  2. dissolution2 g of KH2PO4 --dissolved in tap water
  3. customkept at a temperature of 30° C
  4. washwashed once
  5. customThe cell suspension thus obtained
  6. extractionThe cell-free extract
  7. additionis introduced into a 1 l conical flask
  8. addition1-amino-1-deoxy-D-glucitol (oxalate salt) is added
  9. customto give a concentration of 10 g/l
  10. customis incubated at 30° C. on a rotary shaker at 280 rpm
  11. waitAfter 7 hours it is possible

Sources & evidence

ORD record
ord-b40fa50d009e425eb64a7d156f4d330c
Source dataset
uspto-grants-1981_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04246345

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes