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1. (Article ID: 5597)
Wang M, Zhao Q, Liu W
The versatile low-molecular-weight thiols: Beyond cell protection
BioEssays: News and Reviews in Molecular, Cellular and Developmental Biology 37(12) (2015)
1262-1267
Low-molecular-weight (LMW) thiols are extensively involved in the maintenance of cellular redox potentials and the protection of cells from a variety of reactive chemical and electrophilic species. However, we recently found that the metabolic coupling of two LMW thiols - mycothiol (MSH) and ergothioneine (EGT) - programs the biosynthesis of the anti-infective agent lincomycin A. Remarkably, such a constructive role of the thiols in the biosynthesis of natural products has so far received relatively little attention. We speculate that the unusual thiol EGT might function as a chiral thiolation carrier (for modification) and a novel activator (for glycosylation) of sugar. Additionally, we examine recent evidence for LMW thiols (MSH and others) as sulfur donors of sulfur-containing natural products. Clearly, the LMW thiols have more diverse activities beyond cell protection, and more attention should be paid to the correlation of their functions with thiol-dependent enzymes
ergothioneine, low-molecular-weight thiols, mycothiol, non-Leloir pathway, sulfur incorporation, thiolation carrier
NCBI PubMed ID: 26515639Publication DOI: 10.1002/bies.201500067Journal NLM ID: 8510851Publisher: Hoboken, N.J.: Wiley
Correspondence: wliu
mail.sioc.ac.cn
Institutions: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China, Huzhou Center of Bio-Synthetic Innovation, Huzhou, China
The publication contains the following compound(s):
- Compound ID: 14095
|
Subst-(1-6)-a-Lincosep1S6N7Me-(1-2)-Etg-(1-7)-Sal
Lincose1S6N = thiolincosamide (1,6,8-trideoxy-1-thio-6-amino-D-ery-D-galacto-octose) = SMILES S{1}[C@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O){6}[C@@H]({7}[C@H](O)C)N;
Subst = N-methyl-L-proline = SMILES CN1CCC[C@H]1{1}C(=O)O |
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Structure type: monomer
Trivial name: celesticetin
Compound class: glycoside
Reference(s) to other database(s): GenDB:GQ844764
- Compound ID: 14208
Structure type: monomer
Trivial name: mycothiol
Compound class: glycoside
- Compound ID: 14209
Structure type: monomer
Trivial name: bacillithiol
Compound class: glycoside
- Compound ID: 14094
|
Subst-(1-6)-a-Lincosep1S6N-(1-1)-Me
Lincose1S6N = thiolincosamide (1,6,8-trideoxy-1-thio-6-amino-D-ery-D-galacto-octose) = SMILES S{1}[C@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O){6}[C@@H]([C@H](O)C)N;
Subst = N-methyl-4-propyl-L-proline = SMILES CCC[C@@H]1C[C@@H]({1}C(=O)O)N(C)C1 |
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Structure type: monomer
Trivial name: lincomycin, lincomycin A
Compound class: glycoside
Reference(s) to other database(s): GenDB:EU124663
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