ho oh ho p 2 p - agile biofoundry
TRANSCRIPT
17
Caprolactam
6-Aminocaproic acid
OHO
NH2
O
HN
Glyceraldehyde3-Phosphate
Pentosephosphate pathway
L-ArabinoseD-Xylose
O
OH
OH
OH
HO
OHO
OH
OH
OH
GlucoseL-Arabinose Xylonic acid
1,2,4-Butanetriol
4-Hydroxyvaleric acid
Galactose
1,4-Butanediol
D-XyloseEthylene glycol
Glycolic acid
OOH
OH
OHOH
HO
O
OH
OH
OH
HO
O
OHOH
OH
OH
HO
OHO
OH
OH
OH
D-Erythrose 4-phosphate
3-Phospho-D-glycerate
Phosphoenolpyruvate
Pyruvate
CO2 + H2
Acetyl-CoA
Oxaloacetate
Malate
Glyoxylate
Fumarate
Succinic acidSuccinyl-CoA
ɑ-Ketoglutarate
Ethylene
Isocitrate
cis-Aconitate
Citrate
POO
HO OH
OHO
POHO
O OH
OH
O
OH
POHO
O OH
OH
OHO
O
HOO P
OH
O
OH
O
OH
O
O
S CoA
HO
O
O
OH
O
HO
O
OH
O OH
OH
O
HOO
OHO
OH
O
HOO
OHO
OH
OHO
O
HO OH
O
O
O
HO
O
S CoA
O
HO
O
OH
O
HO
O
OH
O
HO
O
OH
OH
HOOH
OHHO
HOOO
OH
OH
HO
OH
O
OH HOOH
O
OHHO
HO
OHOH
HOOH
O-Phospho-L-serineL-SerineGlycine
5-Aminolevulinate4,5-Dioxopentanoate
Ethanolamine
NH2
HO
O
OOH
O P
O
OH
OH
3-Phosphooxypyruvate
H2N
OO
HO P
O
OH
OHH2N
OH
OOH
H2N
O
OH
O
O
OH
NH2O
OH
O
O
β-Keto acyl-ACP
Malonyl-CoA
Fatty alcohol (C5 or longer)
Alkane(C7 or longer)
Alkene
FAEE
Enoyl-ACP
Malonyl-ACP
Acetyl-ACP
β-Hydroxy acyl-ACP
3-Hydroxypropionic acid
Fatty acids
Adipic acid
3-Pentanone
FAME
Pentadecaheptaene
O
OHHO
O
O
O
O
S CoAHO
OO
S ACPHO
O
O
S ACP
O
S ACPR
O
O
S ACPR
OH
O
S ACPR
O
S ACPRAcyl-ACP
OHR
O
OHR
R
R
O
OH
O
HO
O
OEtR
O
OMeR
Isobutyl acetate
2-Butanone
3-Methyl-1-butanol
Isoamyl acetate
HO
HO
O
Isoprenol
Geraniol Farnesol
Isoprene
Farnesene
Santalene
Pinene Sabinene
Limonene
Myrcene
Artemisinic acid
Bisabolene
Geranylgeraniol
β-Carotene
Astaxanthin
HO
HOO
OH
PO
O
HO
O P
OOH
OH
PO
O
HO
O P
O
HO
OH PO
O
HO
OP
O
OH
HO
PO
O
HO
O P
O
OHOH
OH OH
OH
141615
12
24
2321
22
18
19
25
20
13
11
10
9
87
6
5
4
3
2
1
OO
OH
HO
OOHH H
Mevalonic acid
1,3-Diaminopropane
L-Threonine Homoserine2-Ketobutyric acid
Propionic acid
L-ɑ-Aminocaprolactam
5-Aminopentanamide
5-Aminovaleric acid
Glutaric acid
Cadaverine
L-β-LysineL-Lysine
L-Methionine
Ethylene 1-Aminocyclopropane-1-carboxylic acid
L-Aspartate
Aspartate semialdehyde
L-2-Aminoadipate
L-Homoalanine
2-Methyl-1-butanol
Pimelic acid
Suberic acid
Sebacic acid 7-Hydroxyheptanoic acid
Malonic acid
Valerolactam
Pentanoic acidHeptanoic acid
Butane
Tiglic acid
2-Methylbutyric acid
(E)-2-Methyl-2-pentenoic acid
2-Methylpentanoic acid
Methylmalonyl-CoA
3-Pentanone 5-Methyl-3-hexanone
1-Butanol
3-Methyl-1-pentanol
O
OH
OHO
O
HO
OHOH
NH2
NH2 O
OH
O
HO
O
OH
O
HO
O
OHO
NH2
NH2H2N
NH2
HO
O
OHNH2
OH
OHONH2
OOH
S
O
CoA
OHO O
OH
NH2
S
O
HO
OHO
NH2
HO
O O
S CoA
O
OH
OHO
O
OH
O
OH
O
O
H2NH2N O
OH
H2N NH2
O
HO
O
OH
NH2
NH2
H2N
O
OH OHN
H2N
ONH2
H2N
OOH
H2NO
HN
OOH
OO
OH
O
HO
O OHO
HO
O OH
HO
OOHO
HO
O OHO
HO
Propanol
HO H2N
OOH
L-Isoleucine
Propionyl-CoA
Glutarate semialdehyde
β-Alanine
NH2 O
OH
1,4-Butanediol
4-Hydroxybutyric acid4-Hydroxybutyryl-CoAGamma-butyrolactone
Glycolaldehyde
Ethylene glycol
Glycolic acid
Poly(lactic-co-glycolic acid)
Lactic acid
HO
O
OH
OH
OOH
OHO
HOOH
O
O
O
On m
HOOH
OOH
O
SHO
CoAOO
O
OHHO
4-Hydroxybutyraldehyde
2,3-DihydroxybutyrateO
HO
HOOH
2,4-Dihydroxybutyrate
O
OHHO
OH
1,2,4-Butanetriol
HO
OHOH
O
O
OH
Oxalic acid
β-Hydroxy-ɣ-butyrolactone
OOH
OHO
HO
O
O
Adipic acid
O
OH
O
HO
Succinate semialdehyde
O
OHO
Propionic acid
Levulinic acid6-Hydroxyhexanoic acid
O
OH
O
O
OH
OHO
OH
L-Glutamate
N-Carbamoyl putrescine
N-Acetyl-L-ornithine L-Ornithine
L-Glutamine
Putrescine
Agmatine
Nopaline2-Oxoarginine
Citrulline
L-Arginine
Octopine
Feruloylagmatine
L-1-Pyrroline-5-carboxylate
L-Proline
D-Proline
5-Aminovaleric acid1-Pyrroline-
2-carboxylate
Arginosuccinate
4-Guanidinobutanoate
Proclavaminate
L-Hydroxyproline
Itaconic acid
D-Glucosamine 6-phosphate
4-Aminobutyraldehydeγ-Aminobutyric acid
O
HO
O
OH
NH2HO
OHHO O
PO
O
HO
HO
O
OHH2N
O
O-
HN
NH
H2N
NH2
O
H2N
O
OH
ONH2
O
OHH2N
NH2
O
HO
O
O-
NH
H2N
OHOO
NH2
NH2
O
HO H2NNH2
HN
NH2NH2
OHN O
OH
N
O
O -
NH2HN
O
H2N
O
OH
NH2
HN
NH2
HN
NH2HN
NH
H2N
O
OH
NH
HO
O
HO
N O
O-
HN O
OH
OOH
H2N
HN
NH
H2N
O
O
OH
NHNH
H2N HN
O
OHO
OHO
NO
OH
NH2
O OH
OHO
NH
NH2
N
O OH
H2N
OHO
NH2N
NH2
NH
O
HO
O OH
O
OHHN
NH2N
NH2 O
OH
L-Homocarnosine
γ-Aminobutyric acid
OHO
N
NHNHO
H2N
(R,R)-2,3-Butanediol
(S)-Acetoin (R)-acetoin
(S,S)-2,3-Butanediol
Polylactic acid
Lactyl-CoA Lactic acid
Acrylyl-CoA
Propionyl-CoAPropanol
Acrylic acid
Propionic acid
2-Butanol
Butanone Meso-2,3-Butanediol
Isobutyrate
Isobutyryl-CoA 4-Methylpentanoic acid
Isopentane
2-Ketoisoheptanoate
O
OH
HO
O
OH
OS CoA
OOH
OH
OS CoA
OHO
OH
O
OH
O
S CoA
O
S CoAHO
OH
O
OH
O
OHHO
OHHO
OHHO
OH
O
OH
O
4-methyl-1-pentanol
Acetolactate
3-Methyl-1-butanol
Isobutanol
2-Ketoisocaproate
4-methyl-1-pentanol
Isovalerate
Isocaproate
HO
O
-OO
O
OH
HOO
OH
HO
OHOO
O
HO
O
HO
2-Ketoisovalerate
3-Hydroxyisovalerate
L-Leucine
O
HO OH
NH2
O
HO
L-Valine
NH 2
OHO
Ethanol
AcetaldehydeO
HO
AcetateO
HO
Octanoic acid
O OH
1-Butanol
PentaneHexanoic acid
HO
OOH
O
OHButyrate
Crotonoyl-CoA Butyryl-CoA
Formic acid
Isopropanol
(S)-3-Hydroxybutyryl-CoA
1,3-Butanediol
(R)-3-Hydroxybutyrate
2-Hydroxyisobutyrate
Propane
(R)-3-Hydroxybutyryl-CoA
OO
S CoA
O
HO S CoA
O
HO S CoA
O
S CoA
OHO
HO
O
OH
OH
HO OHHOO
acetone
OHO
Acetoacetyl-CoA
O
On O
O
D-xylono-1,4-lactone
Cineole
Kaurene
Chorismate
Anthranilate
Prephenic acid
L-TyrosineCatechol
L-Tryptophan
4-Hydroxybenzoic acid
Benzyl alcohol
cis, cis-Muconic acid
Dopamine
p-Coumaric acid
p-Hydroxystyrene
Protocatechuic acid
3-Dehydroshikimate3-Deoxy-D-arabino-
heptulosonate-7-phosphate Shikimic acid
Phenylpyruvate
Phenylacetic acid
Phenyl acetaldehyde
L-DOPATyramine
Caffeic acid
Tyrosol
4-Hydroxyphenylacetic acid
4-Hydroxymandelic acid Phenyllactic acid
4-aminophenylacetaldehyde
4-aminophenylalanine
4-aminophenylethanol
6-phenylhexanoate
Poly(3HB-co-PhLA)
L-Phenylalanine
(S)-Mandelate
4-Hydroxyphenyllactic acid
Resveratrol
Toluene
Malonyl-CoA
Benzaldehyde
Phenol
Dihydrobenzenediol
Vanillin
BenzeneFerulic acid
4-phenylbutyrate
HO
HO
OHO
OH
HO
HO
HO
OH
OHO
HO
O
HOO
OH
HO
HO
OO
HO
HO
NH2
OHHO
HO
NH2HO
HO
NH2
OHHO
O
OHOP
O
OHHO O
HO OH
HO
HONH2
O
HO
NH2
ONH2
O
OH
O
HO
HO
HO
HO
HOO
OH OHO
HO
O
OHO
O
HO
NH2
H2NNH2
NH2O
HNOH 2
H2N
H2N
O
-O
NH2
N
O
OH
O
HOOH
O
HO
O
OH
OH
OH
O
HO
NH2HO
HONH2
OHO
HO
O
HO
OH
OH
OHO
HO
OH
OHO
HO OH
O OH
H2N
O
OHO
O
OH
HO
O
O
-O
O
-O
OHO
HO
NH2
OHO
HO
OH
OO-
O
OH
O
HO
O
OHHO
O
O
HO
OHO
SCoA
O
S
O
OHCoA
O*
O
O
*
O
O
O
O
HO
OOH
2-Pyrone-4,6-dicarboxylic acid
Aniline
Danshensu
4-aminocinnamic acid
Serotonin 5-methoxytryptamine
Melatonin
4-Hydroxybenzoate-CoA
Poly(4-hydroxybenzoate)
Phenylethanol
trans-Cinnamic acid
Styrene
Phenylglyoxylate
D-Phenylglycine
Phenethylamine
(R)-Mandelate
L-Phenylglycine
4-Aminobenzoic acid
Isochorismate
Benzoic acid
Hippurate
O
HONH2
NH2
NH
HONH2
NH
O
HN
O
HN
O
H2N
NH
O
O
-O
O
HO
OH
OO-
O
OOH
O
HO
O
SHO
CoA
O
*
O*n
O
OH
OH
O
OHO
NH2
OOH
NH2
OOH
HO
HO
OH
Hydroxytyrosol
4-aminophenylacetic acid
4-aminophenylethylamine
4-aminophenylpyruvate
O
HNOH 2
O
LactaldehydePropanol4-Hydroxyhexan-3-one
Propanal 1,2-Propanediol
1,3-propanediol
Dihydroxyacetone phosphate
3-Hydroxypropanal
4-Hydroxy-2-oxohexanoic acid
Glycerol-3-phosphate
Glycerone
Methylglyoxal
OHO
OO
O
OH
Acetol
HO
O
OH
OHHOO
O
HOO
OH
O
OHAcrylic acid
O
OHHO
3-Hydroxypropionic acid
HO OH O OHOH
HOOH
Glycerol
OHO
OH
D-Glyceraldehyde
OHO
OHHO
D-Glycerate
PO
O
HO
HOO
OH
HO
HO
P
O
O OH
OH
OHO
OH1,3-Propanediol
HO OH
3-Hydroxypropionic acid
O
OHHO
Butyrolactam
ONH
O
OH
OH
OH
HO
L-ArabinoateOH
O
S CoA
p-Coumaroyl-CoA
O
OH
O
HO
β-ketoadipic acid
O
O
O
CitramalateO
HO
O
OH
OHIsobutanol
Isopentenenyldiphosphate
Geranyldiphosphate
Farnesyldiphosphate
Geranylgeranyldiphosphate
Multiple biological reactions Biological reaction
Potential beachhead molecule
Xylitol
HO OH
OH OH
OH
HO
Prenol
HO
BiomassPolysaccharides
This map represents a compilation of metabolic pathways that have been describedfor conversion of biomass-derived polysaccharides to industrial chemicals.Adapted by permission from Springer Nature Customer Service Centre GmbH:Nature, Nature Calalysis, A comprehensive metabolic map for production of bio-based chemicals, Lee, S.Y., et al., 2019
O
OHO
O
ɑ-Ketoglutarate semialdehyde
O
OHO
HO
2-Dehydro-3-deoxy-D-arabinonate
OH
O
OHO
HO
2-Dehydro-3-deoxy-L-arabinonate
OH
O
OH
OH
OH
HO
D-XylonateOH