Chemistry

Synthesizing the Teicoplanin Core

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Science  30 Nov 2001:
Vol. 294, Issue 5548, pp. 1791
DOI: 10.1126/science.294.5548.1791b

The glycopeptide teicoplanin is used clinically, like vancomycin, to combat methicillin-resistant staph infections and is an important target for total synthesis. Teicoplanin shares with vancomycin a macrocyclic tetrapeptide subunit (4-7) that is invariant except for the extent of chlorination of ring 6. However, teicoplanin is more complex than vancomycin, because an asparagine and a leucine are replaced by two arylglycine residues (1, 3) that are more susceptible to racemization and are cross-linked to form a diaryl ether. Evans et al. now report the total synthesis of the tetracyclic teicoplanin core (without the three carbohydrate chains R1, R2, and R3), using a Cu(II)-promoted phenolic arylation reaction to avoid epimerization of the arylglycine residues during macrocycle synthesis.—PDS

J. Am. Chem. Soc., 10.1021/ja011943e.

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