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Enzymatic glycosylation of terpenoids

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Abstract

A significant number of terpenoid compounds are glycosides with the sugars linked to the active groups. Sometimes, the glycosidic residue is crucial for their activity, but in other cases glycosylation only improves pharmacokinetic parameters. Enzymatic glycosylation of terpenoids is a useful tool due to the high selectivity and the mildness of the reaction conditions, in comparison with chemical methods. Several types of biocatalysts have been used in the enzymatic glycosylation of terpenoids. These include the use of glycosyltransferases, trans-glycosidases, and whole-cell biotransformation systems capable of regenerating the cofactor, such as fungi, bacteria, plant-cell cultures, etc. Many biosynthesized terpenoid glycosides display medicinal and pharmacological properties and can be used as pro-drug substances. These terpenoid glycosides have also been employed as food additives (e.g. low-caloric sweetener compounds) and cosmetics, and even have applications as controlled-release fragrances.

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Abbreviations

ATCC:

American type culture collection

CICC:

China center of industrial culture collection

DHA:

Dehydroabietic acid

Gal:

Galactopyranose

GalT:

β-1,4-Galactosyltransferase

GHs:

Glycoside hydrolases

Glc:

Glucopyranose

GTs:

Glycosyltransferases

HeLa:

Human epithelial carcinoma cell line

HIV:

Human immunodeficiency virus

K562:

Human erythromyeloblastoid leukemia cell line

Man:

Mannopyranose

NRRL:

Agricultural research service culture collection (ARS)

POH:

Perillyl alcohol

Rha:

Rhamnopyranose

TGs:

Trans-glycosidases

UDP:

Uridine diphosphate

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Acknowledgments

We thank David Nesbitt for reviewing the English in the manuscript.

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Authors and Affiliations

  1. Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Granada, 18071, Granada, Spain

    Francisco Rivas, Andres Parra, Antonio Martinez & Andres Garcia-Granados

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  1. Francisco Rivas
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  2. Andres Parra
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  3. Antonio Martinez
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  4. Andres Garcia-Granados
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Correspondence to Francisco Rivas or Andres Parra.

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Rivas, F., Parra, A., Martinez, A. et al. Enzymatic glycosylation of terpenoids. Phytochem Rev 12, 327–339 (2013). https://doi.org/10.1007/s11101-013-9301-9

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  • DOI: https://doi.org/10.1007/s11101-013-9301-9

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