Enacyloxins (ENXs) are polyhydroxy-polyenic and yellow-colored antibiotics produced by Frateuria sp. W-315 in a Czapek-Dox medium spent by Neurospora crassa. ENX IIa is a main product and has antibiotic activity against Gram-positive and Gram-negative bacteria. Its mode of action was considered to be an inhibition of peptide biosynthesis, and its inhibition mechanism on the ribosomes was recently reported. Furthermore, ENXs have attracted considerable attention because it showed antibiotic inhibitory activity toward organellar protein synthesis in Plasmodium falciparum. ENX IIa is an enzymatic oxidation product of ENX IVa and both are also converted enzymatically to their decarbamoylated products, dec ENX IIa and dec ENX IVa 4, respectively.
202. "Synthetic Studies of Enacyloxins: a Series of Antibiotics Isolated from Frateuria sp. W-315: C1'-C8' and C9'-C15' Fragments"
　　Aki Saito, Wataru Igarashi, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota, Nat. Prod. Commun., 10 (4), 645-648 (2015).
200. "Facile Synthesis of the Cyclohexane Fragment of Enacyloxins, a Series of Antibiotics Isolated from Frateruria sp. W-315
　　Aki Saito, Wataru Igarashi, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota, Biosci. Biotechnol. Biochem., 78 (5), 766-769 (2014).
156. "Synthesis of C16'-C23' Fragments of Enacyloxins, A Series of Antibiotics from Frateuria sp. W-315"
　　 Wataru Igarashi, Hiroaki Hoshikawa, Hiroyuki Furukawa, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota, Heterocycl. Commun., 17(1-2), 7-9 (2011).
155. "Synthesis of a C9'-C15' Fragment of Enacyloxins, A Series of Antibiotics from Frateuria sp. W-315"
　　 Hiroyuki Furukawa, Hiroaki Hoshikawa, Wataru Igarashi, Manabu Yaosaka, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota, Heterocycl. Commun., 17(1-2), 3-5 (2011).
109. "Setereochemistry of Enacyloxins 4. Completion of Structure Assignment with (13'R, 14'R, 15'S)-Configuration of Enacyloxins, a Series of Antibiotics from Frateuria sp. W-315"
　　 Hiroyuki Furukawa, H. Kiyota, T. Yamada, Manabu Yaosaka, Ryo Takeuchi, Toshihiko Watanabe, S. Kuwahara, Chem. Biodivers., 4, 1601-1604 (2007).
73. "Intramolecular Migration of Long Chain Acyl Group of Enacyloxin IIa Methyl Ester"
　　T. Sugiyama, H. Kiyota, T. Watanabe, T. Oritani, Nat. Prod. Res., 19(6), 581-584 (2005).
48. "Stereochemistry of Enacyloxins 3. (12'S, 17'R, 18'S, 19'R)-Absolute Configuration of the Polyene Part of Enacyloxin IIa (ENX IIa)"
　　R. Takeuchi, H. Kiyota, M. Yaosaka, T. Watanabe, the late T. Sugiyama, T. Oritani, J. Chem. Soc., Perkin Trans. 1, 2001(20), 2676-2681.
44. "Stereochemistry of Enacyloxins 2. Structure Elucidation of Decarbamoyl Enacyloxin IIa and IVa, New Members of Enacyloxin Antibiotics from Frateuria sp. W-315"
　　T. Watanabe, H. Kiyota, R. Takeuchi, K. Enari, T. Oritani, Heterocycl. Commun., 7(4), 313-316 (2001).
43. "Stereochemistry of Enacyloxins 1. Absolute Configurtion of the Cyclohexane Part of Enacyloxins, a Series of Antibiotics from Frateuria sp. W-315"
　　 T. Fujimori, O. Nakayama, H. Kiyota, Y. Kamijima, T. Watanabe, T. Oritani, Heterocycl. Commun., 7(4), 327-330 (2001).

Antimycins

A series of antibiotic antimycins have been isolated from various Streptomyces species since 1946. The curious dilactone structure and strong biological activities has inspired many scientists to investigate their structure activity relationships, mechanism of action and chemical synthesis. We have achieved the total synthesis of (-)-1 and its deformylamidodehydroxy analog (-)-2, and the formal synthesis of (+)-1.

93. "Synthetic Studies on Heterocyclic Antibiotics Containing Nitrogen Atoms" REVIEW
　　H. Kiyota, in "Topic in Heterocyclic Chemistry 06: Bioactive Heterocyles 1", ed. S. Eguchi, Chapter 6, Springer 2006, pp 181-214.
29. "Synthesis and Antimicrobial Activity of Unnatural (-)-Antimycin A3 and its Analog"
　　H. Kondo, T. Oritani and H. Kiyota, Heterocycl. Commun., 6, 211-214 (2000).