煙麴黴醇

化合物

煙麴黴醇(英語:Fumagillol)是一種有機化合物,化學式C16H26O4,屬於一種環氧化合物,存在於Penicillium jensenii英語Penicillium jenseniiPenicillium jensenii[1]煙麴黴Aspergillus fumigatus[2]等真菌中,與其煙麴黴素全合成的重要目標[3][4][5]

煙麴黴醇
英文名 fumagillol
識別
CAS號
PubChem 222778
ChemSpider 193433
SMILES
 
  • CC(=CC[C@@H]1[C@@](O1)(C)[C@H]2[C@@H]([C@@H](CC[C@]23CO3)O)OC)C
InChI
 
  • 1S/C16H26O4/c1-10(2)5-6-12-15(3,20-12)14-13(18-4)11(17)7-8-16(14)9-19-16/h5,11-14,17H,6-9H2,1-4H3/t11-,12-,13-,14-,15+,16+/m1/s1
InChIKey CEVCTNCUIVEQOY-JQOWZUPLSA-N
ChEBI 324935
性質
化學式 C16H26O4
摩爾質量 282.38 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考文獻

  1. ^ Hatanaka, Hiroshi; Kino, Toru; Hashimoto, Michizane; Tsurumi, Yasuhisa; Kuroda, Akio; Tanaka, Hirokazu; Goto, Tosmo; Okuhara, Masakuni. FR65814, a novel immunosuppressant isolated from a Penicillium strain. Taxonomy, fermentation, isolation, physico-chemical and biological characteristics and structure assignment.. The Journal of Antibiotics. 1988, 41 (8): 999–1008. doi:10.7164/ANTIBIOTICS.41.999. 
  2. ^ Lin, HC; Chooi, YH; Dhingra, S; Xu, W; Calvo, AM; Tang, Y. The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene.. Journal of the American Chemical Society. 2013-03-27, 135 (12): 4616–9. PMID 23488861. doi:10.1021/ja312503y. 
  3. ^ Corey EJ, Snider BB. A total synthesis of (+-)-fumagillin. Journal of the American Chemical Society. April 1972, 94 (7): 2549–2550. PMID 5016935. doi:10.1021/ja00762a080. 
  4. ^ Kim D, Ahn SK, Bae H, Choi WJ, Kim HS. An asymmetric total synthesis of (−)-fumagillol. Tetrahedron Letters. 1997, 38 (25): 4437–4440. doi:10.1016/S0040-4039(97)00925-8. 
  5. ^ Vosburg DA, Weiler S, Sorensen EJ. A Concise Synthesis of Fumagillol. Angewandte Chemie. April 1999, 38 (7): 971–974. PMID 29711854. doi:10.1002/(SICI)1521-3773(19990401)38:7<971::AID-ANIE971>3.0.CO;2-W.