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O

CHO CH2OH CH2OH C

H C OH H C OH C O HO C
O
HO C H HO C H HO C H HO C
Chemical Acetobacter Chemical
suboxydans
H C OH H C OH H C OH H C

H C OH H C OH HO C H HO C H

CH2OH CH2OH CH2OH CH2OH

D-Glucose D-Sorbitol L-Sorbose L-Ascorbic acid


(vitamin C)

The biotransformation of sorbitol to sorbose in the H2 C OH H2 C OH


manufacture of ascorbic acid (vitamin C). Polyol dehydrogenase
H C OH C O

H2 C OH H2 C OH

Glycerol Dihdroxyacetone

The biotransformation of glycerol to


dihydroxyacetone.

a polyhydric alcohol. d-Sorbitol is then oxidized to l-


sorbose using Acetobacter suboxydans or Acetobacter
xylinum (Fig. 13.3). Media for this biotransformation
step consist of glucose, yeast extract or corn steep liquor,
Vitamins
a slight excess of calcium carbonate and 15–30% (w/v)
Most vitamins were previously prepared from animal d-sorbitol. The biotransformation is performed at 30°C
and plant tissues, although dried baker’s and brewer’s under vigorous aeration and within 1–2 days a 90–95%
yeast preparations (both are strains of Saccharomyces conversion is achieved (note: a similar biotransforma-
cerevisiae) have long been employed as a rich source of B tion is used for producing dihydroxyacetone, a compo-
vitamins. Microorganisms are now used as sources of a nent of suntanning cosmetics, from glycerol using A.
wide range of these important compounds, including suboxydans or Gluconobacter melanogenus, Fig. 13.4).
thiamin (vitamin B1), riboflavin (vitamin B2), pyridox- l-Sorbose is recovered from the medium following fil-
ine (vitamin B6), cobalamin (vitamin B12), biotin, folic tration and concentration of the filtrate to a syrup. This
acid, l-ascorbic acid (vitamin C), b-carotene (provita- sugar crystallizes on cooling and about 65% is recov-
min A), ergosterol (provitamin D2) and pantothenic ered, based on starting material. The l-sorbose is then
acid. For the production of some vitamins, direct chemically converted to ascorbic acid via 2-keto-l-
fermentation processes are operated, whereas for gluconic acid.
others, biotransformations or combined chemical and A much more direct route from glucose to ascorbic
microbiological processes are employed. acid has now been made possible by the introduction of
a gene encoding 2,5-diketo-d-gluconic acid reductase
from Corynebacterium into Erwinia. This simplifies
Ascorbic acid (vitamin C)
the process to a single biotransformation and a single
Annual production of ascorbic acid is now over 40 000 chemical step. The genetically modified Erwinia strain
tonnes. The established process involves chemical stages transforms glucose to 2-keto-l-gulonic acid (Fig. 13.5),
and a microbial biotransformation. It starts with the which can then be simply converted to ascorbic acid in
chemical catalytic reduction of d-glucose to d-sorbitol, one chemical step.
Reaction steps
The reaction steps are:

• hydrogenation of D-glucose to D-sorbitol, an organic reaction with nickel as a catalyst


under high temperature and high pressure.
• Microbial oxidation or fermentation of sorbitol to L-sorbose with acetobacter [1] at pH 4-6
and 30 °C.
• protection of the 4 hydroxyl groups in sorbose by formation of the acetal with acetone
and an acid to Diacetone-L-sorbose (2,3:4,6−Diisopropyliden−α−L−sorbose)
• Organic oxidation with potassium permanganate followed by heating with water gives
the 2-Keto-L-gulonic acid
• The final step is a ring-closing step or gamma lactonization with removal of water .[2]
• Intermediate 5 can also be prepared directly from 3 with oxygen and platinum

The microbial oxidation of sorbitol to sorbose is important because it provides the correct
stereochemistry.
'Corynebacterium'
Erwinia enzymes 2,5-diketo-D-gluconic acid reductase
D-glucose 2,5-diketo-D-gluconic acid 2-keto-L-gulonic acid

Production of 2-keto-l-gulonic acid by genetically modified strain of Erwinia that expresses 2,5-diketo-d-gluconic acid
reductase from Corynebacterium.

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