The Biochemistry of Sulfonium Compounds

Shapiro, Stuart; Schlenk, F.

doi:10.1002/9780470122679.ch6

Cited by 1 publication

(5 citation statements)

References 190 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…93 For example, DMSP from marine algae serves not only as the major source of reduced sulfur for marine microorganisms, but also as the precursor of dimethylsulfide, the primary sulfur source in the global atmosphere. 94 …”

Section: Thiosugarsmentioning

confidence: 99%

“…Since methionine serves as a precursor for the biosynthesis of SAM, S -methylmethionine, and DMSP, it is possible that methionine is also a precursor in the biosynthesis of salacinol, kotalanol, ponkolanol and salaprinol. 93 …”

Section: Thiosugarsmentioning

confidence: 99%

“…Several well-known sulfonium-containing compounds including SAM, S-methylmethionine, and dimethylsulfoniopropionate (DMSP) play crucial roles in living systems. 93 For example, DMSP from marine algae serves not only as the major source of reduced sulfur for marine microorganisms, but also as the precursor of dimethylsulfide, the primary sulfur source in the global atmosphere. 94 Salacinol (77) 95 and kotalanol (78) 96 isolated from the medicinal herb Salacia reticulate are both naturally occurring thiosugars that contain a sulfonium ion moiety.…”

Section: Group Iii: Thiosugars Containing a Sulfonium Ionmentioning

confidence: 99%

“…124 In this study the authors identified tunA-L (excluding tunM and N) as the minimal set of genes required for tunicamycin biosynthesis. This led to a more reasonable proposal that TunB catalyzes the condensation of uridine ( 89) with UDP-6-deoxy-GalNAc-5,6-ene (93) to yield UDP-N-acetyltunicamine-uracil (91, Scheme 13B). This hypothesis is supported by the finding that a TunB knockout strain accumulates UDP-6-deoxy-GlcNAc-5,6-ene in culture media.…”

Section: Tunicamine Containing Nucleoside Antibioticsmentioning

confidence: 99%

“…It appears that the orientation of the nicotinamide ring in TunA, which places C-4 of NAD + toward C-4 of UDP-GlcNAc and away from C-6, serves as a ''regioselective switch'' that determines the identity of the product. On the basis of these results, a biosynthetic pathway was put forward in which UDP-6-deoxy-GalNAc-5,6-ene (93), produced from UDP-GlcNAc (87) by the successive oxidation and epimerization reactions of TunA and TunF, is joined with the 5 0 -uridine radical (94) by TunB (with possible involvement of TunM) to give UDP-N-acetyltunicamine-uracil (91, Scheme 13B). 125 It was also proposed that epimerization of UDP-6-deoxy-GlcNAc-5,6-ene (92) to UDP-6-deoxy-GalNAc-5,6-ene (93) by TunF is needed to place s*(C8 0 -O8 0 ) LUMO to be parallel to C7 0 SOMO in 7 0 -UDP-N-acetyltunicamine-uracil, thereby stabilizing this transient radical intermediate (95).…”

Section: Tunicamine Containing Nucleoside Antibioticsmentioning

confidence: 99%

See 4 more Smart Citations

The biosynthesis of nitrogen-, sulfur-, and high-carbon chain-containing sugars

2013

View full text Add to dashboard Cite

Carbohydrates serve many structural and functional roles in biology. While the majority of monosaccharides are characterized by the chemical composition: (CH2O)n, modifications including deoxygenation, C-alkylation, amination, O- and N-methylation, which are characteristic of many sugar appendages of secondary metabolites, are not uncommon. Interestingly, some sugar molecules are formed via modifications including amine oxidation, sulfur incorporation, and “high-carbon” chain attachment. Most of these unusual sugars have been identified over the past several decades as components of microbially produced natural products, although a few high-carbon sugars are also found in the lipooligosaccharides of the outer cell walls of Gram-negative bacteria. Despite their broad distribution in nature, these sugars are considered “rare” due to their relative scarcity. The biosynthetic steps that underlie their formation continue to perplex researchers to this day and many questions regarding key transformations remain unanswered. This review will focus on our current understanding of the biosynthesis of unusual sugars bearing oxidized amine substituents, thio-functional groups, and high-carbon chains.

show abstract

Section: Thiosugarsmentioning

confidence: 99%

Section: Thiosugarsmentioning

confidence: 99%