[Unusual amidation reaction of Asn-containing glycopeptide antibiotics using the coupling reagent PyBOP].

E N Olsuf'eva, S E Solov'eva, M I Reznikova, A M Korolev, M N Preobrazhenskaia
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Abstract

The coupling reagent PyBOP is widely used for the synthesis of different peptides and their amides, particularly for carboxamides of glycopeptide antibiotics of vancomycin or teicoplanin groups. The amidation reaction of the peptide core of the glycopeptide antibiotic eremomycin (I) with highly reactive amines in the presence of PyBOP is usually not accompanied by the formation of side products. However, the amidation of I with bulky amines (e.g., decyl amine and adamantyl amine) in the presence of PyBOP and Et3N or di-(i-Pr)2EtN (pH - 8.5) yielded N-unsubstituted carboxamide of eremomycin (Ia) as an admixture. The reaction of (I) or vancomycin (II) with an excess of PyBOP and Et3N (pH - 8.5) without addition of an amine or ammonia gave a mixture of products which contained higher amounts of the corresponding N-unsubstituted carboxamides (-20%). The structures of the samples of Ia and vancomycin amide (IIa) were proved by 1H NMR and ESI MS methods and confirmed by comparing with the authentic samples.

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[偶联剂PyBOP对含砷糖肽抗生素的异常酰胺化反应]。
偶联试剂PyBOP广泛用于合成各种多肽及其酰胺,特别是万古霉素或替可普兰蛋白类糖肽类抗生素的羧胺。在PyBOP存在下,糖肽类抗生素eremomycin (I)的肽核与高活性胺的酰胺化反应通常不伴有副产物的形成。然而,在PyBOP和Et3N或二(I - pr)2EtN (pH - 8.5)存在的情况下,用大体积胺(例如,癸胺和金刚烷胺)酰胺化I,得到作为混合物的n -未取代的伊雷霉素(Ia)羧酰胺。(I)或万古霉素(II)与过量的PyBOP和Et3N (pH - 8.5)反应,而不添加胺或氨,得到的混合物中相应的n -未取代的羧酰胺含量较高(-20%)。通过1H NMR和ESI MS对Ia和万古霉素酰胺(IIa)的结构进行了验证,并与正品进行了对比。
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