ケンドマイシン

ケンドマイシン[1]
	IUPAC名 (1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one
	系統名 (1R,9S,10S,12S,14E,16S,19R,20R,21S,22R)-3,9,21-Trihydroxy-5,10,12,14,16,20,22-heptamethyl-23,24-dioxatetracyclo[17.3.1.16,9.02,7]tetracosa-2,5,7,14-tetraen-4-one
	別称 (−)-TAN 2162
識別情報
CAS登録番号	59785-91-0
PubChem	5472093
ChemSpider	4582118
MeSH	C485395
ChEMBL	CHEMBL523927
	SMILES C[C@H]\1CC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)C3=C(C(=O)C(=C4C3=C[C@@](O4)([C@H](C[C@@H](C/C(=C1)/C)C)C)O)C)O)C)O)C;
	InChI InChI=1S/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 Key: HKLDUJXJTQJSEJ-OLXNOMCWSA-N; InChI=1/C29H42O6/c1-14-8-9-22-18(5)24(30)19(6)28(34-22)23-21-13-29(33,17(4)12-16(3)11-15(2)10-14)35-27(21)20(7)25(31)26(23)32/h10,13-14,16-19,22,24,28,30,32-33H,8-9,11-12H2,1-7H3/b15-10+/t14-,16+,17-,18-,19+,22+,24-,28+,29+/m0/s1 Key: HKLDUJXJTQJSEJ-OLXNOMCWBE;
特性
化学式	C29H42O6
モル質量	486.64 g mol−1
外観	黄色粉末
DMSO、メタノールへの溶解度	可溶
危険性
主な危険性	Toxic
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

ケンドマイシン（Kendomycin）は、Streptomyces violaceoruberから最初に単離された抗がん性マクロライドである[2]。エンドセリン受容体アンタゴニストおよび抗骨粗鬆症剤としての強力な活性を有している[3]。また、様々な腫瘍細胞株に対して強い細胞毒性を有している[2]。

全合成

その強力な生物学的活性のため、ケンドマイシンは全合成の標的として関心を集めている。ケンドマイシンの最初の全合成は2004年にLeeとYuanによって達成された[4][5][6][7][8][9]。

出典

Kendomycin Archived 2008-05-16 at the Wayback Machine. at Alexis-Biochemicals
H B Bode; A Zeeck (2000). “Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces”. J. Chem. Soc. Perkin Trans. 1 323 (3): 323–328. doi:10.1039/a908387a.
Burke Research Group Archived 2006-08-29 at the Wayback Machine. University of Wisconsin
Yu Yuan; Hongbin Men; Chulbom Lee (2004). “Total Synthesis of Kendomycin: A Macro−C−Glycosidation Approach”. J. Am. Chem. Soc. 126 (45): 14720–14721. doi:10.1021/ja0447154. PMC 1785127. PMID 15535687.
A B Smith III; E F Mesaros; E Meyer (2006). “Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy”. J. Am. Chem. Soc. 128 (15): 5292–9. doi:10.1021/ja060369+. PMID 16608366.
J T Lowe; J S Panek (2008). “Total Synthesis of (−)-Kendomycin”. Org. Lett. 10 (17): 3813–6. doi:10.1021/ol801499s. PMID 18698784.
K B Bahnck; S D Rychnovsky (2008). “Formal Synthesis of (−)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle”. J. Am. Chem. Soc. 130 (13): 177. doi:10.1021/ja805187p. PMC 2697922. PMID 18767844.
Magauer, Thomas; Martin, Harry J.; Mulzer, Johann (2009). “Total Synthesis of the Antibiotic Kendomycin by Macrocyclization using Photo-Fries Rearrangement and Ring-Closing Metathesis”. Angewandte Chemie International Edition 48 (33): 6032–6. doi:10.1002/anie.200900522. PMID 19350596.
Martin, Harry J.; Magauer, Thomas; Mulzer, Johann (2010). “In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin”. Angewandte Chemie International Edition 49 (33): 5614–26. doi:10.1002/anie.201000227. PMID 20818753.

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[1] Kendomycin Archived 2008-05-16 at the Wayback Machine. at Alexis-Biochemicals

[Bode-2] H B Bode; A Zeeck (2000). “Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces”. J. Chem. Soc. Perkin Trans. 1 323 (3): 323–328. doi:10.1039/a908387a.

[3] Burke Research Group Archived 2006-08-29 at the Wayback Machine. University of Wisconsin

[4] Yu Yuan; Hongbin Men; Chulbom Lee (2004). “Total Synthesis of Kendomycin: A Macro−C−Glycosidation Approach”. J. Am. Chem. Soc. 126 (45): 14720–14721. doi:10.1021/ja0447154. PMC 1785127. PMID 15535687.

[5] A B Smith III; E F Mesaros; E Meyer (2006). “Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy”. J. Am. Chem. Soc. 128 (15): 5292–9. doi:10.1021/ja060369+. PMID 16608366.

[6] J T Lowe; J S Panek (2008). “Total Synthesis of (−)-Kendomycin”. Org. Lett. 10 (17): 3813–6. doi:10.1021/ol801499s. PMID 18698784.

[7] K B Bahnck; S D Rychnovsky (2008). “Formal Synthesis of (−)-Kendomycin Featuring a Prins-Cyclization to Construct the Macrocycle”. J. Am. Chem. Soc. 130 (13): 177. doi:10.1021/ja805187p. PMC 2697922. PMID 18767844.

[8] Magauer, Thomas; Martin, Harry J.; Mulzer, Johann (2009). “Total Synthesis of the Antibiotic Kendomycin by Macrocyclization using Photo-Fries Rearrangement and Ring-Closing Metathesis”. Angewandte Chemie International Edition 48 (33): 6032–6. doi:10.1002/anie.200900522. PMID 19350596.

[9] Martin, Harry J.; Magauer, Thomas; Mulzer, Johann (2010). “In Pursuit of a Competitive Target: Total Synthesis of the Antibiotic Kendomycin”. Angewandte Chemie International Edition 49 (33): 5614–26. doi:10.1002/anie.201000227. PMID 20818753.