Water → (1S,2R,19R,22R,34S,37R,40R,52S)-2,64-bis[[(2R,3S,4R,5S,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-22-amino-5,15-dichloro-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

10 g of teicoplanin complex (i.e. the antibiotic complex containing teichomycin factors A1, A2 and A3, as obtained by fermentation of strain ATCC 31121 according to U.S. Pat. No. 4,239,751; the water content determined by Karl-Fischer method is 10.5% by weight) is suspended in 100 ml of 0.5 N hydrogen chloride solution in 1,1,1,3,3,3-hexafluoro-2-propanol and the suspension is heated at 70° C. with stirring while continuously bubbling anhydrous hydrogen chloride for 20 hours. Then the reaction mixture is worked up as in Example 11 yielding 3.8 g of substantially pure deglucoteicoplanin. From 0.8 g of this sample are obtained 0.5 g of crystalline pure deglucoteicoplanin by employing the procedure described in the last part of Example 1.

Provenance & Evidence