И так. Меня заинтересовала эта тема и было принято решение собрать информацию по брожению.
Итак, ФАК действительно восстанавливаестя в диол. Но почему то сразу диол из БА никто не получает. Почему? Загадка. Так что брожение БА прямо в диол не миф
https://pubs.acs.org/doi/pdf/10.1021/ed072p2771-Phenylpropane-1,2-diol, PhCHOH.CHOH.CH3, was originally isolated in two
racemic forms, ~-, m.p. 57~ and fl-, m.p. 93 ~ from 1,2-dibromo-l-phenylpropane.
Both forms gave phenylacetone when boiled with dilute sulphuric acid, and phenyl-
methylglyoxal when oxidised with nitric acid (Zincke and K. Zahn, Ber., 1910, 43,
849). Optically active forms have been obtained from inactive benzoylmethylmethanol
by reduction with fermenting yeast (C. Neuber9 and W. Komarewsky, Biochem. Z.,
1927, 182, 287; F. yon Falkenhausen, ibid., 1930, 219, 242, 24
It is well known that the reduction of 1-phenylpropane-1,2-dione 47 medi-
ated by baker’s yeast gives (1R,2S)-1-phenylpropanediol 50 in excellent yield
and ee,41 through a mechanism involving consecutive reactions where both
Cao bonds are reduced. 42 as a consequence, two interesting reaction inter-
mediates were detected (scheme 10.10).
there are different biocatalytic approaches for the synthesis of enantio-
merically enriched intermediate (R)-49, known as L-paC, that are of partic-
ular value for the pharmaceutical industry and as fine chemicals because
of their utility as building blocks for the production of larger molecules.43
one of these approaches is a whole cell redox process catalyzed by several
microorganisms, including the bio-oxidation of 1,2-diols. For this approach,
a protocol of bio-oxidation of (1R,2S)-50 mediated by whole cells of S. cerevi-
siae was developed, giving (S)-48 in high ee in aerobic conditions, and also a
protocol of kinetic resolution of (±)-anti-50 was developed to obtain (1S,2R)-
50 in high ee using resting cells of microorganisms, among then Geotrichum
candidum (scheme 10.11).
xperimental Procedure
In a 2-L Erlenmeyer flask, 40 g of freeze-dried
bakers' yeast is suspended in 0.5 L of water. To this
add 500 mg of 1-phenyl-1,2-propanedione,and stir
the mixture a t room temperature for 1h.
85 (m, 1H); 7.91 to 8.10 (m, 2H).
After 1 h of stirring, filter the mixture on Celite 545 al-
ready prepared. The flask is washed with the minimum
quantity of water (about 50 mLJ and 50 mL of ether. Satu-
rate the filtrate with sodium chloride (140 g), and extract
with ether2 ( 3 x 60 mLJ. The organic layer i s dried on
MgS04. During the extraction, an emulsion can occur. If so,
MgS04 is added.