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Comment
. 2015 Jul 10;349(6244):149.
doi: 10.1126/science.aaa9626. Epub 2015 Jul 9.

ORGANIC SYNTHESIS. Response to Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence"

Zhiqiang Ma  1 , Xiaolei Wang  1 , Xiao Wang  2 , Rodrigo A Rodriguez  3 , Curtis E Moore  4 , Shuanhu Gao  2 , Xianghui Tan  2 , Yuyong Ma  2 , Arnold L Rheingold  4 , Phil S Baran  3 , Chuo Chen  2
Affiliations
Comment

ORGANIC SYNTHESIS. Response to Comment on "Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence"

Zhiqiang Ma et al. Science. .

Abstract

Sherman et al. commented on the precedence of enantiodivergence, listing a number of congeneric natural products with opposite chirality. However, these "congeners" are not derived from enantiodivergent biosyntheses. Instead, they are antipodes arising from separate enantiomeric biosyntheses. A distinct feature of the biosynthesis of the cyclic pyrrole-imidazole dimers is the production of antipodal congeners without the corresponding enantiomers.

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Figures

Fig. 1
Fig. 1. Enantiodivergent versus enantiomeric biosyntheses
Enantiodivergent biosynthesis (A) leads to the formation of antipodal congeners, whereas enantiomeric biosynthesis (B) produces enantiomers.
Fig. 2
Fig. 2. Biosynthetic pathways for the reverse prenylated indole alkaloids
(A) Brevianamides A and B arise from enantiomeric biosynthesis. (B) Paraherquamide A and VM55599 arise from diastereomeric biosynthesis.
See this image and copyright information in PMC

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References

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