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Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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Biochemical and Structural Characterization of the Carbohydrate Transport Substrate-binding-protein SP0092

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Published on: October 2, 2017

Structure revision of asperjinone using computer-assisted structure elucidation methods.

Mikhail Elyashberg¹, Kirill Blinov, Sergey Molodtsov

¹Advanced Chemistry Development, Moscow Department, 6 Akademik Bakulev Street, Moscow 117513, Russian Federation.

Journal of Natural Products

|January 8, 2013

Summary

This summary is machine-generated.

The structure of natural product asperjinone was revised using the Structure Elucidator expert system. Comparison with similar compounds confirmed the new structure, correcting previous findings.

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Area of Science:

Natural Product Chemistry
Computational Chemistry
Organic Chemistry

Background:

Asperjinone is a natural product isolated from thermophilic Aspergillus terreus.
Previous structural elucidation of asperjinone (1) required revision.

Purpose of the Study:

To revise the elucidated structure of asperjinone (1).
To confirm the reliability of the revised structure (2).

Main Methods:

Utilized the expert system Structure Elucidator for structural revision.
Compared the revised structure with 180 known structures containing the (3,3-dimethyloxiran-2-yl)methyl fragment (3).

Main Results:

The structure of asperjinone (1) was revised to a new structure (2).
Chemical shifts of known compounds contradicted the initially suggested structure (1).
The revised structure (2) demonstrated reliability through comparative analysis.

Conclusions:

The Structure Elucidator expert system successfully revised the asperjinone structure.
The revised structure (2) is a more accurate representation of the natural product.
This study highlights the importance of computational tools in natural product chemistry.