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Vitamin c

Vitamin c

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Published by Mozhi Arasu

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Published by: Mozhi Arasu on Apr 08, 2011
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11/27/2013

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Vitamins
Most vitamins were previously prepared from animaland plant tissues, although dried baker’s and brewer’syeast preparations (both are strains of 
Saccharomycescerevisiae
) have long been employed as a rich source of Bvitamins. Microorganisms are now used as sources of awide range of these important compounds, includingthiamin (vitamin B
1
), riboflavin (vitamin B
2
), pyridox-ine (vitamin B
6
), cobalamin (vitamin B
12
), biotin, folicacid,
l
-ascorbic acid (vitamin C),
b
-carotene (provita-min A), ergosterol (provitamin D
2
) and pantothenicacid. For the production of some vitamins, directfermentation processes are operated, whereas forothers, biotransformations or combined chemical andmicrobiological processes are employed.
Ascorbic acid (vitamin C)
Annual production of ascorbic acid is now over 40000tonnes. The established process involves chemical stagesand a microbial biotransformation. It starts with thechemical catalytic reduction of 
d
-glucose to
d
-sorbitol,a polyhydric alcohol.
d
-Sorbitol is then oxidized to
l
-sorbose using
Acetobacter suboxydans
or
Acetobacterxylinum
(Fig. 13.3). Media for this biotransformationstep consist of glucose, yeast extract or corn steep liquor,a slight excess of calcium carbonate and 15–30% (w/v)
d
-sorbitol. The biotransformation is performed at 30°Cunder vigorous aeration and within 1–2 days a 90–95%conversion is achieved (note: a similar biotransforma-tion is used for producing dihydroxyacetone, a compo-nent of suntanning cosmetics, from glycerol using
A.suboxydans
or
Gluconobacter melanogenus
, Fig. 13.4).
l
-Sorbose is recovered from the medium following fil-tration and concentration of the filtrate to a syrup. Thissugar crystallizes on cooling and about 65% is recov-ered, based on starting material. The
l
-sorbose is thenchemically converted to ascorbic acid via 2-keto-
l
-gluconic acid.A much more direct route from glucose to ascorbicacid has now been made possible by the introduction of a gene encoding 2,5-diketo-
d
-gluconic acid reductasefrom
Corynebacterium
into
Erwinia.
This simplifiesthe process to a single biotransformation and a singlechemical step. The genetically modified
Erwinia
straintransforms glucose to 2-keto-
l
-gulonic acid (Fig. 13.5),which can then be simply converted to ascorbic acid inone chemical step.
CHOH HHH
D
-Glucose
D
-Sorbitol
L
-Sorbose
L
-Ascorbic acid(vitamin C)HC CCCCCH
2
OHCH
2
OH CH
2
OHCH
2
OHCH
2
OHCH
2
OHOH OHHCCCHOOOOOH H C OH H C HHCOHOH H C OHHO HCHOHCHOCHOCHOCHOChemical Chemical
Acetobacter suboxydans
The biotransformation of sorbitol to sorbose in themanufacture of ascorbic acid (vitamin C).
H
2
CCOHH
2
COHOHH
Glycerol Dihdroxyacetone
Polyol dehydrogenase
H
2
CCOHH
2
COHO
The biotransformation of glycerol todihydroxyacetone.
 
Reaction steps
The reaction steps are:
 
hydrogenation of 
D
-glucose to
D
-sorbitol, an organic reaction with nickel as a catalystunder high temperature and high pressure.
 
Microbial oxidation or fermentation of sorbitol to
L
-sorbose with acetobacter
[1]
at pH 4-6and 30 °C.
 
protection of the 4 hydroxyl groups in sorbose by formation of the acetal with acetoneand an acid to Diacetone-L-sorbose (2,3:4,6
Diisopropyliden
α
L
sorbose)
 
Organic oxidation with potassium permanganate followed by heating with water givesthe 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 platinumThe microbial oxidation of sorbitol to sorbose is important because it provides the correctstereochemistry.

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