Toward a Stable Apoptolidin Derivative: Identification of Isoapoptolidin and Selective Deglycosylation of Apoptolidin

Organic Letters

Volumn 4, Issue 22, 2002, Pages 3823-3825

  Pennington, James D ^a   Williams, Howard J ^a   Salomon, Arthur R ^b   Sulikowski, Gary A ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; APOPTOLIDIN; MACROLIDE; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATE SYNTHASE;

ARTICLE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; DRUG STABILITY; FERMENTATION; GLYCOSYLATION; IC 50; ISOMERISM; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; DRUG STABILITY; FERMENTATION; GLYCOSYLATION; INHIBITORY CONCENTRATION 50; ISOMERISM; MACROLIDES; MITOCHONDRIAL PROTON-TRANSLOCATING ATPASES; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0038341710     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026829v     Document Type: Article

References (16)

1. (a) Hayakawa, Y.; Kim, J. W.; Adachi, H.; Shin-ya, K.; Fujita, K.; Seto, H. J. Am. Chem. Soc. 1998, 120, 3524-3525.
2. (b) Kim, J. W.; Adachi, H.; Shin, Y. K.; Hayakawa, Y.; Seto, H. J. Antibiot. 1997, 50, 628-630.
3. (a) Salomon, A. R.; Voehringer, D. W.; Herzenberg, L. A.; Khosla, C. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14766-14771.
4. (b) Salomon, A. R.; Voehringer, D. W.; Herzenberg, L. A.; Khosla, C. Chem. Biol. 2001, 8, 71-80.
5. (a) Nicolaou, K. C.; Li, Y.; Fylaktakidou, K. C.; Mitchell, H. J.; Wei, H. X.; Weyershausen, B. Angew. Chem., Int. Ed. 2001, 40, 3849-3854.
6. (b) Nicolaou, K. C.; Li, Y. W.; Fylaktakidou, K. C.; Mitchell, H. J.; Sugita, K. Angew. Chem., Int. Ed 2001, 40, 3854-3857.
7. For other synthetic studies toward apoptolidin: (a) Nicolaou, K. C.; Li, Y.; Weyerhausen, B.; Wei, H.-x. J. Chem. Soc., Chem. Commun. 2000, 307-308. (b) Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621-624. (c) Sulikowski, G. A.; Lee, W. M.; Jin, B.; Wu, B. Org. Lett. 2000, 2, 1439-1442. (d) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873-8876.
8. For other synthetic studies toward apoptolidin: (a) Nicolaou, K. C.; Li, Y.; Weyerhausen, B.; Wei, H.-x. J. Chem. Soc., Chem. Commun. 2000, 307-308. (b) Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621-624. (c) Sulikowski, G. A.; Lee, W. M.; Jin, B.; Wu, B. Org. Lett. 2000, 2, 1439-1442. (d) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873-8876.
9. For other synthetic studies toward apoptolidin: (a) Nicolaou, K. C.; Li, Y.; Weyerhausen, B.; Wei, H.-x. J. Chem. Soc., Chem. Commun. 2000, 307-308. (b) Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621-624. (c) Sulikowski, G. A.; Lee, W. M.; Jin, B.; Wu, B. Org. Lett. 2000, 2, 1439-1442. (d) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873-8876.
10. For other synthetic studies toward apoptolidin: (a) Nicolaou, K. C.; Li, Y.; Weyerhausen, B.; Wei, H.-x. J. Chem. Soc., Chem. Commun. 2000, 307-308. (b) Schuppan, J.; Ziemer, B.; Koert, U. Tetrahedron Lett. 2000, 41, 621-624. (c) Sulikowski, G. A.; Lee, W. M.; Jin, B.; Wu, B. Org. Lett. 2000, 2, 1439-1442. (d) Toshima, K.; Arita, T.; Kato, K.; Tanaka, D.; Matsumura, S. Tetrahedron Lett. 2001, 42, 8873-8876.
11. Synthesis of apoptolidinone: Schuppan, J.; Wehlan, H.; Keiper, S.; Koert, U. Angew. Chem., Int. Ed 2001, 40, 2063-2066.
12. Salomon, A. R.; Zhang, Y. B.; Seto, H.; Khosla, C. Org. Lett. 2001, 3, 57-59.
13. Fermentation and isolation was conducted at Stanford University by A. Gulledge and O. Jankowski (Wender group) and A. Salomon (Khosla group).
14. Under similar conditions, apoptolidin decomposed in less than 12 h. The peracetylated psuedoaglycone 4 underwent successive deacetylation via transesterifications leading to decomposition after 56 h.
15. Assay was performed as previously described; see refs 2b and 6.
16. We cannot distinguish whether isoapoptolidin or apoptolidin is first produced biosynthetically and subsequently isomerize by an acyl shift to the other under the fermentation conditions. In other words, isoapoptolidin may very well be the first-formed natural product that isomerizes to apoptolidin.