Erythromycin → 12-Deoxyerythronolide A

HRID 638150Notes

Reaction equation

[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H]2O[C@@H](C)[C@H](O)[C@@](OC)(C)C2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1(O)[CH3:50].C[C@H]1O[C@@H](O[C@@H]2[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@@]3(OC3)C[C@@H]2C)[C@H](O)[C@@H](N(C)C)C1>>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([OH:20])[C@H:13]([CH3:32])[C@@H:12]([OH:33])[C@@:11]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@H:4]1[CH3:50]

Participants

Reactant 2

HCID 12560Erythromycin

HCID 72493oleandomycin

Product 1

HCID 44111312-Deoxyerythronolide A

Procedure

Under HPLC the peak corresponding to P 15153 has a retention time with respect to erythromycin A of 0.64 and with respect to oleandomycin of 0.99. For the above four antibiotics, which are obtained in admixture from erythronolide B, after 100 hours of fermentation and before the isolation, the total antibiotic activity, expressed as activity of erythromycin A, is about 120-150 mcg/ml.

Sources & evidence

ORD record: ord-8883402084254e478ea08728ad68667c
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04560662

Reaction notes

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