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Scalemic natural products.

Sarah Mazzotta1, Vincenzo Rositano1,2, Luca Senaldi2

  • 1Dipartimento di Chimica, UniversitĂ  degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy.

Natural Product Reports
|July 13, 2023
PubMed
Summary
This summary is machine-generated.

Scalemic natural products, often with multiple stereocenters, arise from specific enzyme actions or degradation, not just imprecise enzyme activity. This review examines their generation and analytical uses.

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Area of Science:

  • Natural Product Chemistry
  • Organic Chemistry
  • Biochemistry

Background:

  • Scalemic natural products exhibit low optical purity despite multiple stereogenic centers.
  • Their formation is mechanistically complex, involving distinct biogenetic steps.
  • This phenomenon is not typically due to imprecise enzyme function.

Purpose of the Study:

  • To critically review the mechanisms behind the generation of scalemic natural products.
  • To identify enzymatic processes leading to scalemic states.
  • To discuss analytical applications of natural product scalemicity.

Main Methods:

  • Literature review of studies up to 2022.
  • Analysis of enzymatic and spontaneous reaction pathways.
  • Examination of antipodal enzyme expression and optical purity erosion.

Main Results:

  • Scalemic states result from antipodal enzymes or erosion of optical purity.
  • Enzymatic reactions and spontaneous degradation are key mechanisms.
  • Evidence supports these processes over general enzymatic imprecision.

Conclusions:

  • Understanding scalemic natural product formation requires considering specific enzymatic strategies and degradation pathways.
  • Analytical methods can exploit the unique properties of scalemic compounds.
  • Further research can elucidate complex biogenetic pathways.