Chemistry Reference
In-Depth Information
(a)
OCH
3
O
OH
O
O
OH
O
O
HO
19
O
O
HO
O
O
O
O
O
O
O
O
O
OH
O
OH
OH
OH
29
28 nanchangmycin
(b)
4 Malonyl CoA
9 MMCoA
NanA1-A10
O
O
OH
OH
O
OH
O
O
NanO
Malonyl CoA
ACP
Nan10
-S
30
O
OH
OH
O
OH
OH
ACP-S
ACP-S
NanI
O
O
O
O
O
OH
O
O
O
O
O
O
O
OH
H
31
32
NanG1-G4
NanM
4-
O
-methyl-L-rhodinose
D-glc-1-P
O
OH
OH
1. NanA11
2. NanE
3. NanP
HO
O
O
28
O
O
O
O
NanG5
OH
OH
33 apo-nanchangmycin
(c)
(d)
(e)
(f)
(
+
)
(
−
)
OH
O
OH
O
OO
N
O
HO
2
C
C
7
H
15
R
OH
OH
S
O
O
O
O
O
O
OH
HO
34
(
−
)-nonactic acid: R = CH
3
35
(
−
)-Homononactic acid: R = C
2
H
5
34
36
37
(g)
O
O
OO
OO
O
O
OO
O
2
C
KS
KS
−
CoA
KS
+
SCoA
CoAS
HO
CoAS
CoAS
SCoA
−
CoA
−
CoA
CoAS
CO
2
O
CO
2
OO
41
O
38
39
40
O
KR, KR
OH
OH
OH
OH
COSCoA
COSCoA
(6
S
, 8
S
)- 42a
(6
R
, 8
R
)- 42b
(
+
)
(
−
)
(
−
)
NonS
NonL
??
NonL
O
O
HO
O
O
O
O
O
OH
O
OH
O
NonJ
O
O
NonK
O
O
SCoA
SCoA
O
−
CoA
O
O
O
−
CoA
O
O
CoAS
43a
(
−
)-nonactate
43b
(
+
)-nonactate
O
O
(
−
)
(
)
(
+
)
+
5 nonactin
44
Figure 8.3
(a) Nanchangmycin and novel nanchangmycin aglycone. (b) Nanchangmycin
biosynthesis (19, 20). (Adapted from Reference 17 with permission from the Royal
Society of Chemistry.) (c) Structure of building blocks for the macrotetrolides. (d) Biosyn-
thetic origin of carbon skeleton of nonactic acid (21). (e) (2,3-
13
C
2
)-3-ketoadipate
N
-
caprylcysteamine thioester (22). (f) Homochiral nonactate dimmer (23). (g) Nonactin
biosynthesis (21). (Adapted from Reference 17 with permission from the Royal Society
of Chemistry.)
