Kanamycin → (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HRID 1765925Notes

Reaction equation

N[C@H](C(O)=[O:11])CC1C=CC=CC=1.C1C(N)=NC(=O)N([C@@H]2O[C@H](COP(OCCCCCCCCCCCCCCCC(O)=O)(O)=O)[C@@H](O)[C@@H]2O)C=1.CC1(C)S[C@@H]2[C@H](NC([C@H](N)C3C=CC=CC=3)=O)C(=O)N2[C@H]1C(O)=O.C1[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]([O:96][C@H:97]2[O:102][C@H:101]([CH2:103][OH:104])[C@@H:100]([OH:105])[C@H:99](N)[C@H:98]2[OH:107])[C@@H]1N>>[O:104]=[CH:103][C@@H:101]([C@H:100]([C@@H:99]([C@@H:98]([CH2:97][OH:96])[OH:107])[OH:11])[OH:105])[OH:102]

Participants

Reactant 4

HCID 6032Kanamycin

HCID 6140L-Phenylalanine

HCID 6249Ampicillin

HCID 131037Pca 16

Product 1

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Procedure

Two strains (designated as WWQ51.1 and WSQ1) were constructed from the E. coli phenylalanine overproducing strain E. coli NST74 by transformation with pCA16 and pKSM-pdc1 and selection for ampicillin and kanamycin resistance, as described in Example 4. Since preliminary experiments showed similar patterns for both constructs, we chose strain WWQ51.1 for further studies.

Sources & evidence

ORD record: ord-020b9a2552d84b3cbea21ca7de791de7
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229806B2

Reaction notes

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