Lycospidine A, a New Type of Lycopodium Alkaloid from Lycopodium complanatum

Lycospidine A (1), the first example of a Lycopodium alkaloid which contains an unprecedented five-membered A ring, was isolated from Lycopodium complanatum. The unique five-membered A ring in 1 indicates that carbons 2–5 in 1 are presumably derived from proline instead of the lysine biosyntheticall...

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Published inOrganic letters Vol. 15; no. 10; pp. 2438 - 2441
Main Authors Cheng, Jin-Tang, Liu, Fei, Li, Xiao-Nian, Wu, Xing-De, Dong, Liao-Bin, Peng, Li-Yan, Huang, Sheng-Xiong, He, Juan, Zhao, Qin-Shi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.05.2013
Amer Chemical Soc
Subjects
Alkaloids - chemistry
Chemistry
Chemistry, Organic
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - isolation & purification
Lycopodium - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Physical Sciences
Science & Technology
BIOSYNTHESIS
HUPERZINE-A
SKELETON
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Summary:Lycospidine A (1), the first example of a Lycopodium alkaloid which contains an unprecedented five-membered A ring, was isolated from Lycopodium complanatum. The unique five-membered A ring in 1 indicates that carbons 2–5 in 1 are presumably derived from proline instead of the lysine biosynthetically, which suggests that 1 represent a new class of Lycopodium alkaloid. In addition, the unique structural feature and biosynthetic origin of 1 shed new insight into the structural diversity of Lycopodium alkaloid analogue libraries potentially accessible by engineered biosynthesis.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol400907v