Lemonomycin

Lemonomycin
Names
	Other names (–)-Lemonomycin
Identifiers
3D model (JSmol)	Interactive image ;
ChEBI	CHEBI:211916 ;
ChemSpider	8730105 ;
PubChem CID	10554716 ;
	InChI InChI=1S/C27H41N3O9/c1-11-21(31)13-8-16-20-14(26(34)35)7-15(28-20)25(33)30(16)17(19(13)22(32)23(11)37-6)10-38-18-9-27(3,36)24(29(4)5)12(2)39-18/h12,14-18,20,24-26,28,33-36H,7-10H2,1-6H3/t12-,14+,15-,16-,17-,18+,20+,24+,25-,27-/m0/s1 Key: JXWCEWIDCYAQRW-RNWDBXQFSA-N;
	SMILES C[C@H]1[C@H]([C@@](C[C@@H](O1)OC[C@H]2C3=C(C[C@@H]4N2[C@H]([C@@H]5C[C@H]([C@H]4N5)C(O)O)O)C(=O)C(=C(C3=O)OC)C)(C)O)N(C)C;
Properties
Chemical formula	C27H41N3O9
Molar mass	551.637 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated June 01, 2025

Lemonomycin is an antibiotic with the molecular formula C₂₇H₄₁N₃O₉ which is produced by the bacterium Streptomyces candidus .^[1]^[2] Lemonomycin was first isolated in 1964^[2] Lemonomycin has also shown activity against human colon tumor cells.^[2]

References

↑ Ashley, Eric R.; Cruz, Ernest G.; Stoltz, Brian M. (1 December 2003). "The Total Synthesis of (−)-Lemonomycin". Journal of the American Chemical Society. 125 (49): 15000–15001. doi:10.1021/ja039223q. PMID 14653730.
1 2 3 Williams, Robert M. (2 December 2012). 19th International Congress on Heterocyclic Chemistry: Book of Abstracts. Newnes. p. 130. ISBN 978-0-08-098401-8.

Jiménez-Somarribas, Alberto; Williams, Robert M. (2 September 2013). "Synthetic studies on lemonomycin: construction of the tetracyclic core". Tetrahedron. 69 (35): 7505–7512. doi:10.1016/j.tet.2013.05.009. hdl: 10217/80986 . ISSN 0040-4020. PMC 4114395 . PMID 25083002.
Harmata, Michael (2012). Strategies and Tactics in Organic Synthesis. Academic Press. p. 353. ISBN 978-0-12-386540-3.
Gholamzadeh, Parisa (14 January 2019). The Pictet–Spengler Reaction: A Powerful Strategy for the Synthesis of Heterocycles. Advances in Heterocyclic Chemistry. Vol. 127. Academic Press. p. 157. doi:10.1016/bs.aihch.2018.09.002. ISBN 978-0-12-817150-9. S2CID 104840386.

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[1] Ashley, Eric R.; Cruz, Ernest G.; Stoltz, Brian M. (1 December 2003). "The Total Synthesis of (−)-Lemonomycin". Journal of the American Chemical Society. 125 (49): 15000–15001. doi:10.1021/ja039223q. PMID 14653730.

[Streptomyces-2] 1 2 3 Williams, Robert M. (2 December 2012). 19th International Congress on Heterocyclic Chemistry: Book of Abstracts. Newnes. p. 130. ISBN 978-0-08-098401-8.

[1]

[2]

Names

Other names (–)-Lemonomycin
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:211916
ChemSpider	8730105
PubChem CID	10554716
InChI InChI=1S/C27H41N3O9/c1-11-21(31)13-8-16-20-14(26(34)35)7-15(28-20)25(33)30(16)17(19(13)22(32)23(11)37-6)10-38-18-9-27(3,36)24(29(4)5)12(2)39-18/h12,14-18,20,24-26,28,33-36H,7-10H2,1-6H3/t12-,14+,15-,16-,17-,18+,20+,24+,25-,27-/m0/s1 Key: JXWCEWIDCYAQRW-RNWDBXQFSA-N
SMILES C[C@H]1[C@H]([C@@](C[C@@H](O1)OC[C@H]2C3=C(C[C@@H]4N2[C@H]([C@@H]5C[C@H]([C@H]4N5)C(O)O)O)C(=O)C(=C(C3=O)OC)C)(C)O)N(C)C
Properties
Chemical formula	C₂₇H₄₁N₃O₉
Molar mass	551.637 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lemonomycin

References

Further reading