Accessorizing natural products: Adding to nature's toolbox

Lamb, Sherry S.; Wright, Gerard D.

doi:10.1073/pnas.0408858102

Cited by 26 publications

(12 citation statements)

References 11 publications

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“…As a consequence, only the combination of fold and sequence determines the binding properties of a protein and thus enables the enormous number of different functions to be carried out by a limited number of folds [25, 61 -63]. As revealed by SCONP, the number of scaffolds explored by natural products is also limited and conserved (see previous section) [64]. However, the implementation of different substitution patterns of the scaffold leads in the end to a vast number of possible compounds.…”

Section: Kaiser Et Almentioning

confidence: 99%

Biology-inspired synthesis of compound libraries

Kaiser

Wetzel

Kumar

et al. 2008

Cell. Mol. Life Sci.

148

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Section: Kaiser Et Almentioning

confidence: 99%

Biology-inspired synthesis of compound libraries

Kaiser

Wetzel

Kumar

et al. 2008

Cell. Mol. Life Sci.

148

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“…Siderophores have previously been suggested as drug delivery vehicles [31,39]. Other peptide drugs might be targeted for uptake by bacterial siderophore receptors using C-terminal modification analogous to that in MccE392m.…”

Section: C-glycosyl Peptide Siderophoresmentioning

confidence: 99%

“…It was shown that the IroB protein was the only enzyme required to switch siderophore production from enterobactin to salmochelin S4 [29]. Salmochelins 8 -10 Walsh et al have purified and characterized the Cglycosyltransferase IroB from E. coli CFT073, the first time that C-glycosyltransferase activity has been reconstituted in vitro [30,31]. They showed that IroB catalyzes the transfer of one, two or three glucopyranose groups from UDP-Glc to enterobactin, with a k cat of about 10 min -1 for the first Cglycosylation.…”

Section: C-glycosyl Peptide Siderophoresmentioning

confidence: 99%

Bioactive C-Glycosides from Bacterial Secondary Metabolism

Hultin

2005

CTMC

126

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C-Glycosides are commonly regarded as unusual structures, but they are far more prevalent among natural products than is imagined. This review discusses the C-glycosidic compounds produced by various bacteria, particularly the "biosynthetically talented" Streptomyces. The major structure types are presented, along with brief descriptions of the known biological and pharmacological properties of the compounds. Recent work has uncovered the genetic basis for the biosynthesis of several bacterial C-glycosides, and emphasis is placed on those cases where it has been possible to identify (at least provisionally) the C-glycosyltransferase in the pathway. Prospects for biosynthetic engineering, combinatorial biosynthesis, or glycorandomization in C-glycosidic natural products are briefly discussed.

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“…Glycosylation is important for the biological activity of macrolide, peptide and aminoglycoside antibioticsas well as numerous anticancer, antiparasitic, and antifungal agents of diverse biosynthetic origin (Lamb and Wright, 2005; Mendez and Salas, 2001; Walsh et al, 2003). These sugar residues play crucial biological roles in many natural products and their removal oftentimes results in the loss of biological activity (Mendez and Salas, 2001; Thorson et al, 2001; Weymouth-Wilson, 1997).…”

Section: Introductionmentioning

confidence: 99%

Chapter 21 Enzymatic Synthesis of TDP-Deoxysugars

White-Phillip

Thibodeaux

Liu

2009

Methods in Enzymology

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Many biologically active bacterial natural products contain highly modified deoxysugar residues that are often critical for the activity of the parent compounds. Most of these deoxysugars are secondary metabolites that are biosynthesized in the form of nucleotide diphosphate (NDP) sugars prior to their transfer to natural product aglycones by glycosyltransferases. Over the past decade, many biosynthetic pathways that lead to the formation of these unusual sugars have been unraveled, and the mechanisms of many key enzymatic transformations involved in these pathways have been elucidated. However, obtaining workable quantities of NDP-deoxysugars for in vitro studies is often a difficult task. This limitation has hindered an in-depth investigation of the substrate specificity of deoxysugar biosynthetic enzymes, many of which are promiscuous with respect to their NDP-sugar substrates and are, thus, potentially useful catalysts for natural product glycoengineering. Presented in this review are procedures for the enzymatic synthesis and purification of a variety of NDP-deoxysugars, including some early intermediates in NDP-deoxysugar biosynthetic pathways, and highly modified NDP-deoxysugars that are late intermediates in their respective biosynthetic pathways. The procedures described herein could be used as general guidelines for the development of specific protocols for the synthesis of other NDP-deoxysugars.

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Accessorizing natural products: Adding to nature's toolbox

Cited by 26 publications

References 11 publications

Biology-inspired synthesis of compound libraries

Biology-inspired synthesis of compound libraries

Bioactive C-Glycosides from Bacterial Secondary Metabolism

Chapter 21 Enzymatic Synthesis of TDP-Deoxysugars

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