Fed-Batch Bioproduction of Spectinomycin
9
OH
f
\
140
OH
OH
[ OxJdoreduetase ]
OH
~lp
D- GLUCOSE
HO " ~
"OH
HO
OH
OH
MYO - INOS1TOL
4 - KETO - 6 - DEOXY -
D - GLUCOSE
l
'
~
CH3
OH H
NH 2
~
/
O
ACTINOSPECrOSE
1, 3 - MYO - INOSADIAMINE "-&
o
,
Methylation
HO / ~
~0-/'] y
'•
NH =
OH O
CH 3 OH
I .//.._
DESMETHYL SPECTINOMYEqN
HfN /~ ~.~ OH
I
.o- y .o,
J ~,,.,~o,, J
ACTINAMINE
CH 3 OH
/N ~..~
~_~y~o 0
CH 3
H
HO ~O~/j
Possible
/
, it
H/N~cH 3
OH O
"~
ratelimiting
steps
SPECTINOMYCIN
Fig. 1. Biosynthetic pathway for spectinomycin
conversion to 4-keto-6-deoxy-D-glucose. The first pathway continues from myoinositol to form 1,3-myo-inosadiamine, then actinamine and finally spectinomycin. The intermediate 4-keto-6-deoxy-o-glucose of the second pathway
forms actinospectose and then spectinomycin. Two intermediates of these alternate pathways, 1,3-myo-inosadiamine and actinospectose, also combine to give