Benzene → 16846-24-5

HRID 1109840Notes

Reaction equation

HRID 1109840 reaction equation
CCCC[CH2:5][CH3:6].C1C=CC=CC=1.S(=O)(=O)(O)[OH:14].[CH3:18][C@H:19]1[O:35][C:33](=[O:34])[CH2:32][C@@H:31]([OH:36])[C@H:30]([O:37][CH3:38])[C@@H:29]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[C@@H:43]([O:47][C@@H:48]3[O:53][C@@H:52]([CH3:54])[C@H:51]([O:55][C:56]([CH2:58][CH:59]([CH3:61])[CH3:60])=[O:57])[C@@:50]([OH:63])([CH3:62])[CH2:49]3)[C@H:42]([N:64]([CH3:66])[CH3:65])[C@H:41]2[OH:67])[C@@H:28]([CH2:68][CH:69]=[O:70])[CH2:27][C@@H:26]([CH3:71])[C@@H:25]([OH:72])[CH:24]=[CH:23][CH:22]=[CH:21][CH2:20]1>C(OCC)(=O)C.CO>[CH3:18][C@H:19]1[O:35][C:33](=[O:34])[CH2:32][C@@H:31]([O:36][C:5]([CH3:6])=[O:14])[C@H:30]([O:37][CH3:38])[C@@H:29]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[C@@H:43]([O:47][C@@H:48]3[O:53][C@@H:52]([CH3:54])[C@H:51]([O:55][C:56]([CH2:58][CH:59]([CH3:60])[CH3:61])=[O:57])[C@@:50]([OH:63])([CH3:62])[CH2:49]3)[C@H:42]([N:64]([CH3:66])[CH3:65])[C@H:41]2[OH:67])[C@@H:28]([CH2:68][CH:69]=[O:70])[CH2:27][C@@H:26]([CH3:71])[C@@H:25]([OH:72])[CH:24]=[CH:23][CH:22]=[CH:21][CH2:20]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 8058HexaneHCID 5282322Leucomycin A1

Product 1

HCID 528216516846-24-5

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

After developing the plate in a developer composed of n-hexane:benzene:methanol:ethyl acetate=30:10:25:8:20, and product spots were tested by color development with sulfuric acid to try to detect 3-acylated leucomycin A1. As a result, it was found that from among about 200 transformed strains, Streptomyces lividans 53A strain (hereafter, referred to as "strain 53A") produced leucomycin A3, i.e., 3-O-acetyl leucomycin A1. The leucomycin produced by the strain 53A was identified to be leucomycin A3 from results of analyses of TLC, HPLC, UV spectrum, NMR spectrum, antibacterial spectrum and the like.

Sources & evidence

ORD record
ord-3625a2499cd949a28dfdde69788c61b7
Source dataset
uspto-grants-1994_06
Patent number
US05322937

Reaction notes

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