Total Syntheses of Vancomycin-Related Glycopeptide Antibiotics and Key Analogues

Overview

Journal Chem Rev

Publisher American Chemical Society

Specialty Chemistry

Date 2017 Apr 25

PMID 28437097

Citations 59

Authors

Akinori Okano

Nicholas A Isley

Dale L Boger

Affiliations

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Abstract

A review of efforts that have provided total syntheses of vancomycin and related glycopeptide antibiotics, their agylcons, and key analogues is provided. It is a tribute to developments in organic chemistry and the field of organic synthesis that not only can molecules of this complexity be prepared today by total synthesis but such efforts can be extended to the preparation of previously inaccessible key analogues that contain deep-seated structural changes. With the increasing prevalence of acquired bacterial resistance to existing classes of antibiotics and with the emergence of vancomycin-resistant pathogens (VRSA and VRE), the studies pave the way for the examination of synthetic analogues rationally designed to not only overcome vancomycin resistance but provide the foundation for the development of even more powerful and durable antibiotics.

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References

Ge M, Chen Z, Onishi H, Kohler J, Silver L, Kerns R . Vancomycin derivatives that inhibit peptidoglycan biosynthesis without binding D-Ala-D-Ala. Science. 1999; 284(5413):507-11. DOI: 10.1126/science.284.5413.507. View

Nicolaou , Boddy , Brase , Winssinger . Chemistry, Biology, and Medicine of the Glycopeptide Antibiotics. Angew Chem Int Ed Engl. 1999; 38(15):2096-2152. DOI: 10.1002/(sici)1521-3773(19990802)38:15<2096::aid-anie2096>3.0.co;2-f. View

Candiani G, Abbondi M, Borgonovi M, Romano G, Parenti F . In-vitro and in-vivo antibacterial activity of BI 397, a new semi-synthetic glycopeptide antibiotic. J Antimicrob Chemother. 1999; 44(2):179-92. DOI: 10.1093/jac/44.2.179. View

Goldman R, Baizman E, Longley C, Branstrom A . Chlorobiphenyl-desleucyl-vancomycin inhibits the transglycosylation process required for peptidoglycan synthesis in bacteria in the absence of dipeptide binding. FEMS Microbiol Lett. 2000; 183(2):209-14. DOI: 10.1111/j.1574-6968.2000.tb08959.x. View

Healy V, Lessard I, Roper D, Knox J, WALSH C . Vancomycin resistance in enterococci: reprogramming of the D-ala-D-Ala ligases in bacterial peptidoglycan biosynthesis. Chem Biol. 2000; 7(5):R109-19. DOI: 10.1016/s1074-5521(00)00116-2. View

Macfarlane D, Stibbe J, Kirby E, ZUCKER M, Grant R, McPherson J . Letter: A method for assaying von Willebrand factor (ristocetin cofactor). Thromb Diath Haemorrh. 1975; 34(1):306-8. View

Li H, Jiang X, Ye Y, Fan C, Romoff T, Goodman M . 3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization. Org Lett. 2000; 1(1):91-3. DOI: 10.1021/ol990573k. View

Losey H, Peczuh M, Chen Z, Eggert U, Dong S, Pelczer I . Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides. Biochemistry. 2001; 40(15):4745-55. DOI: 10.1021/bi010050w. View

Ma C, Liu X, Li X, Yu S, Cook J . Efficient asymmetric synthesis of biologically important tryptophan analogues via a palladium-mediated heteroannulation reaction. J Org Chem. 2001; 66(13):4525-42. DOI: 10.1021/jo001679s. View

10.

Boger D, Kim S, Mori Y, Weng J, Rogel O, Castle S . First and second generation total synthesis of the teicoplanin aglycon. J Am Chem Soc. 2001; 123(9):1862-71. DOI: 10.1021/ja003835i. View

11.

Singh S, Jayasuriya H, Salituro G, ZINK D, Shafiee A, Heimbuch B . The complestatins as HIV-1 integrase inhibitors. Efficient isolation, structure elucidation, and inhibitory activities of isocomplestatin, chloropeptin I, new complestatins, A and B, and acid-hydrolysis products of chloropeptin I. J Nat Prod. 2001; 64(7):874-82. DOI: 10.1021/np000632z. View

12.

Boger D . Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001; 21(5):356-81. DOI: 10.1002/med.1014. View

13.

Boger D, Zhou J, Borzilleri R, Nukui S, Castle S . Synthesis of (9R,12S)- and (9S,12S)-Cycloisodityrosine and Their N-Methyl Derivatives. J Org Chem. 1997; 62(7):2054-2069. DOI: 10.1021/jo961346o. View

14.

Wang W, Kong F . New Synthetic Methodology for Regio- and Stereoselective Synthesis of Oligosaccharides via Sugar Ortho Ester Intermediates. J Org Chem. 2001; 63(17):5744-5745. DOI: 10.1021/jo981135e. View

15.

Boger D, Castle S, Miyazaki S, Wu J, Beresis R, Loiseleur O . Vancomycin CD and DE Macrocyclization and Atropisomerism Studies. J Org Chem. 2001; 64(1):70-80. DOI: 10.1021/jo980880o. View

16.

Evans D, Katz J, Peterson G, Hintermann T . Total synthesis of teicoplanin aglycon. J Am Chem Soc. 2001; 123(49):12411-3. DOI: 10.1021/ja011943e. View

17.

Zasloff M . Antimicrobial peptides of multicellular organisms. Nature. 2002; 415(6870):389-95. DOI: 10.1038/415389a. View

18.

Kobayashi H, Shin-Ya K, Nagai K, Suzuki K, Hayakawa Y, Seto H . Neuroprotectins A and B, bicyclohexapeptides protecting chick telencephalic neuronal cells from excitotoxicity. I. Fermentation, isolation, physico-chemical properties and biological activity. J Antibiot (Tokyo). 2002; 54(12):1013-8. DOI: 10.7164/antibiotics.54.1013. View

19.

Kobayashi H, Shin-Ya K, Furihata K, Nagai K, Suzuki K, Hayakawa Y . Neuroprotectins A and B, bicyclohexapeptides protecting chick telencephalic neurons from excitotoxicity. II. Structure determination. J Antibiot (Tokyo). 2002; 54(12):1019-24. DOI: 10.7164/antibiotics.54.1019. View

20.

Walsh T, Howe R . The prevalence and mechanisms of vancomycin resistance in Staphylococcus aureus. Annu Rev Microbiol. 2002; 56:657-75. DOI: 10.1146/annurev.micro.56.012302.160806. View