Biosynthesis of phoslactomycins: Cyclohexanecarboxylic acid as the starter unit

Tetrahedron

Volumn 59, Issue 38, 2003, Pages 7465-7471

  Sekiyama, Yasuyo ^a   Palaniappan, Nadaraj ^b   Reynolds, Kevin A ^b   Osada, Hiroyuki ^a  

^a Japan Science and Technology Agency   (Japan)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

Biosynthesis; Cyclohexanecarboxylic acid; Phoslactomycin; Phosphatase inhibitor

Indexed keywords

CARBON 13; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; PHOSLACTOMYCIN A; PHOSLACTOMYCIN B; PHOSLACTOMYCIN C; PHOSLACTOMYCIN D; PHOSLACTOMYCIN DERIVATIVE; PHOSLACTOMYCIN E; PHOSLACTOMYCIN F; POLYKETIDE; POLYKETIDE SYNTHASE; SHIKIMIC ACID;

ACTINOMYCES; ACYLATION; ANTIBIOTIC BIOSYNTHESIS; ARTICLE; BACTERIAL STRAIN; CIS TRANS ISOMERISM; FERMENTATION; HYDROXYLATION; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STAINING; STREPTOMYCES;

ACTINOBACTERIA (CLASS);

EID: 0041328960     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01205-5     Document Type: Article

References (38)

1. Moore B.S., Hertweck C. Nat. Prod. Rep. 19:2002;70-99.
2. Sattler I., Thiericke R., Zeeck A. Nat. Prod. Rep. 15:1998;221-240.
3. (a) Vezina C., Kudelski A., Sehgal S.N. J. Antibiot. 28:1975;721-726
4. (b) Sehgal S.N., Baker H., Vezina C. J. Antibiot. 28:1975;727-732
5. (c) Dumont F.J., Su Q.X. Life Sci. 58:1995;373-395.
6. (a) Kino T., Hatanaka H., Hashimoto M., Nishiyama M., Goto T., Okuhara M., Kohsaka M., Aoki H., Imanaka H. J. Antibiot. 40:1987;1249-1255
7. (b) Kino T., Hatanaka H., Miyata S., Inamura N., Nishiyama M., Yajima T., Goto T., Okuhara M., Kohsaka M., Aoki H., Ochiai T. J. Antibiot. 40:1987;1256-1265
8. (c) Tanaka H., Kuroda A., Marusawa H., Hatanaka H., Kino T., Goto T., Hashimoto M., Taga T. J. Am. Chem. Soc. 109:1987;5031-5033.
9. Hippchen B., Roll A., Poralla K. Arch. Microbiol. 129:1981;53-55.
10. (a) Fushimi S., Nishikawa S., Shimazu A., Seto H. J. Antibiot. 42:1989;1019-1025
11. (b) Fushimi S., Furihata K., Seto H. J. Antibiot. 42:1989;1026-1036.
12. Tomiya T., Uramoto M., Isono K. J. Antibiot. 43:1990;118-121.
13. (a) Ozasa T., Suzuki K., Sasamata M., Tanaka K., Kobori M., Kadota S., Nagai K., Saito T., Watanabe S., Iwanami M. J. Antibiot. 42:1989;1331-1338
14. (b) Ozasa T., Tanaka K., Sasamata M., Kaniwa H., Shimizu M., Matsumoto H., Iwanami M. J. Antibiot. 42:1989;1339-1343.
15. (a) Tunac J.B., Graham B.D., Dobson W.E. J. Antibiot. 36:1983;1595-1600
16. (b) Stampwala S.S., Bunge R.H., Hurley T.R., Willmer N.E., Brankiewicz A.J., Steinman C.E., Smitka T.A., French J.C. J. Antibiot. 36:1983;1601-1605
17. (c) Hokanson G.C., French J.C. J. Org. Chem. 50:1985;462-466
18. (d) Walsh A.H., Cheng A., Honkanen R.E. FEBS Lett. 416:1997;230-234.
19. Usui T., Marriott G., Inagaki M., Swarup G., Osada H. J. Biochem. 125:1999;960-965.
20. (a) Kohama T., Enokita R., Okazaki T., Miyaoka H., Torikata A., Inukai M., Kaneko I., Kagasaki T., Sakaida Y., Satoh A., Shiraishi A. J. Antibiot. 46:1993;1503-1511
21. (b) Kohama T., Nakamura T., Kinoshita T., Kaneko I., Shiraishi A. J. Antibiot. 46:1993;1512-1519.
22. Kawada M., Kawatsu M., Masuda T., Ohba S., Amemiya M., Kohama T., Ishizuka M., Takeuchi T. Int. Immunopharmacol. 3:2003;179-188.
23. Shibata T., Kurihara S., Yoda K., Haruyama H. Tetrahedron. 51:1995;11999-12012.
24. Moore B.S., Cho H., Casati R., Kennedy E., Reynolds K.A., Mocek U., Beale J.M., Floss H.G. J. Am. Chem. Soc. 115:1993;5254-5266.
25. Cropp T.A., Wilson D.J., Reynolds K.A. Nat. Biotechnol. 18:2000;980-983.
26. Moore B.S., Poralla K., Floss H.G. J. Am. Chem. Soc. 115:1993;5267-5274.
27. Wallace K.K., Reynolds K.A., Koch K., McArthur H.A.I., Brown M.S., Wax R.G. J. Am. Chem. Soc. 116:1994;11600-11601.
28. Reynolds K.A., Wallace K.K., Handa S., Brown M.S., McArthur H.A.I., Floss H.G. J. Antibiot. 50:1997;701-703.
29. Lowden P.A.S., Böhm G.A., Staunton J., Leadlay P.F. Angew. Chem. Int. Ed. 35:1996;2249-2251.
30. Lowden P.A.S., Wilkinson B., Böhm G.A., Handa S., Floss H.G., Leadlay P.F., Staunton J. Angew. Chem. Int. Ed. 40:2001;777-779.
31. The amount of the labeled PLMs obtained from labeled precursors was indicated in parenthesis as a percentage of that of entire analog pool.
32. Willaert J.J., Lemière G.L., Dommisse R.A., Lepoivre J.A., Alderweireldt F.C. Bull. Soc. Chim. Belg. 93:1984;139-149.
33. Willaert J.J., Lemière G.L., Dommisse R.A., Lepoivre J.A., Alderweireldt F.C. J. Chem. Res. Minipr. 7:1985;2401-2423.
34. Ohtsuka Y., Oishi T. Chem. Pharm. Bull. 36:1988;4722-4736.
35. (a) Orere D.M., Reese C.B. J. Chem. Soc., Chem. Commun. 1977;280-281
36. (b) Jiricny J., Orere D.M., Reese C.B. J. Chem. Soc., Perkin Trans. 1. 1980;1487-1492.
37. Pojer P.M. Tetrahedron Lett. 25:1984;2507-2508.
38. Palaniappan N., Kim B.S., Sekiyama Y., Osada H., Reynolds K.A. J. Biol. Chem. 2003;. in press.