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L-Tryptophan → Aspoxicillin

HRID 658076
Notes
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Reaction equation

HRID 658076 reaction equation
[CH3:1][C:2]1([CH3:34])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH:21][C:22]([C@H:24]([NH2:30])[CH2:25][C:26]([NH:28][CH3:29])=[O:27])=[O:23])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:31]([OH:33])=[O:32].N[C@H](C(O)=O)CC1C2C(=CC=CC=2)NC=1.CC(S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)C.[CH:65]1[CH:70]=[C:69]2[C:71]([CH2:74][C@@:75]([OH:85])([C:82]([OH:84])=[O:83])[CH2:76][C@H:77]([NH2:81])[C:78]([OH:80])=[O:79])=[CH:72][NH:73][C:68]2=[CH:67][CH:66]=1>>[CH3:1][C:2]1([CH3:34])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH:21][C:22]([C@H:24]([NH2:30])[CH2:25][C:26]([NH:28][CH3:29])=[O:27])=[O:23])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:31]([OH:33])=[O:32].[CH:65]1[CH:70]=[C:69]2[C:71]([CH2:74][C@@:75]([OH:85])([C:82]([OH:84])=[O:83])[CH2:76][C@H:77]([NH2:81])[C:78]([OH:80])=[O:79])=[CH:72][NH:73][C:68]2=[CH:67][CH:66]=1.[NH:73]1[C:68]2[C:69](=[CH:70][CH:65]=[CH:66][CH:67]=2)[C:71]([CH2:74][C:75](=[O:85])[C:82]([O-:84])=[O:83])=[CH:72]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6305L-TryptophanHCID 71961AspoxicillinHCID 656894isopropyl beta-D-thiogalactopyranoside2×HCID 9860847Monatin

Product 3

HCID 71961AspoxicillinHCID 5460337
3-(1H-Indol-3-yl)-2-oxopropanoate
HCID 9860847Monatin

Procedure

The aspC and the proA genes were cloned into the pTrc99a expression vector (Amersham, Piscataway, N.J.). The resulting vector was transformed into the tryptophan auxotrophs CAG18455 or CAG18579 (see Example 4 for strain descriptions). The transformants were plated on M9 minimal medium with 0.1 mM IPTG and 5 mM monatin. After 3 days at 37° C., the strains with the operon plasmids formed colonies, while the parent strains did not appear to grow. Additionally, the growth was dependent on the presence of IPTG indicating that expression of the operon was required for growth. In this complementation study, the aspC/proA operon formed MP from monatin and indole-3-pyruvate from MP. The indole-3-pyruvate could then be converted to L-tryptophan allowing the tryptophan auxotrophs to grow on M9 minimal medium.

Workup

  1. customthe strains with the operon plasmids formed colonies

Sources & evidence

ORD record
ord-f062741798b34a1a946fb3caa575d6e0
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08076108B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes