Synthetic approach toward antibiotic tunicamycins — VI total synthesis of tunicamycins

Suami, Tetsuo; Sasai, Hiroaki; Matsuno, Kazuhiro; Suzuki, Nobuo; Fukuda, Yoshimasa; Sakanaka, Osamu

doi:10.1016/s0040-4039(01)81486-6

Cited by 40 publications

(16 citation statements)

References 16 publications

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“…10 Suami et al. applied a Henry condensation to form the C5′C6′ bond and a Koenigs–Knorr‐type glycosylation to construct the C11′OC1′′ linkage, but both the elaboration of the 5′‐hydroxy group from the nitroaldol adduct and the formation of the β,α‐11′,1′′‐trehalose were non‐stereoselective and low‐yielding 9b,c. Myers et al.…”

Section: Methodsmentioning

confidence: 99%

A Modular Approach to the Total Synthesis of Tunicamycins

2015

Angewandte Chemie

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The tunicamycins constitute a delicate mimic of the bisubstrate intermediates of N‐acetyl‐D‐hexosamine‐1‐phosphate translocases and thus inhibit bacterial cell‐wall synthesis and the N glycosylation of eukaryotic proteins. An efficient approach to the synthesis of this unique type of nucleoside antibiotics is now reported and features the assembly of five modules in a highly stereoselective and robust manner. A Mukaiyama aldol reaction, intramolecular acetal formation, gold(I)‐catalyzed O and N glycosylation, and final N acylation were used as the key steps.

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Section: Methodsmentioning

confidence: 99%

A Modular Approach to the Total Synthesis of Tunicamycins

2015

Angewandte Chemie

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“…Chemical synthesis has played a large role in understanding the binding modes of these compounds by generating derivatives to test in inhibition experiments. Because of the complex chemical structures of all classes of natural product-based nucleoside antibiotics, only few reports describe efforts towards the total synthesis of nucleoside antibiotics, including muraymycin (Tanino et al 2010;, tunicamycin (Suami et al 1983(Suami et al , 1984Myers et al 1991, 1993a, 1993b, Li and Yu 2015, and pacidamycin (Okamoto et al 2012b). Rather, chemists have started with the minimal scaffolds needed to obtain binding, and have elaborated on these using various methods.…”

Section: Chemical Approaches To Analogs Of Nucleoside Antibioticsmentioning

confidence: 99%

Bacterial phosphoglycosyl transferases: initiators of glycan biosynthesis at the membrane interface

2017

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Phosphoglycosyl transferases (PGTs) initiate the biosynthesis of both essential and virulence-associated bacterial glycoconjugates including lipopolysaccharide, peptidoglycan and glycoproteins. PGTs catalyze the transfer of a phosphosugar moiety from a nucleoside diphosphate sugar to a polyprenol phosphate, to form a membrane-bound polyprenol diphosphosugar product. PGTs are integral membrane proteins, which include between 1 and 11 predicted transmembrane domains. Despite this variation, common motifs have been identified in PGT families through bioinformatics and mutagenesis studies. Bacterial PGTs represent important antibacterial and virulence targets due to their significant role in initiating the biosynthesis of key bacterial glycoconjugates. Considerable effort has gone into mechanistic and inhibition studies for this class of enzymes, both of which depend on reliable, high-throughput assays for easy quantification of activity. This review summarizes recent advances made in the characterization of this challenging but important class of enzymes.

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“…83) Much attentions have been focused on the synthesis of tunicamycins because of their unique structure. [84][85][86][87][88][89][90][91] We thought that SmI 2 -promoted aldol reaction can also be applied to the synthesis of tunicaminyluracil, a core structure of tunicamycins (Chart 7). Namely, aldol reaction between a phenylthioketone derivative 45 and a uridine 5Ј-aldehyde derivative 46 would provide an aldol product 47.…”

Section: Total Synthesis Of Herbicidin Bmentioning

confidence: 99%

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

Ichikawa

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Synthetic nucleoside chemistry based on nucleoside natural products synthesis were described. First, a samarium diiodide (SmI 2 )-promoted aldol reaction with the use of a a-phenylthioketone as an enolate was developed. The characteristics of this reaction are that the enolate can be regioselectively generated and the aldol reaction proceeds under near neutral condition. This reaction is proved to be a powerful reaction for the synthesis of complex nucleoside natural products, and herbicidin B and fully protected tunicaminyluracil, which were undecose nucleoside natural products, were synthesized. Next, the synthetic methodology of the caprazamycins, which are promising antibacterial nucleoside natural products, was also developed by the strategy including b bselective ribosylation without using a neighboring group participation. Our synthetic route provided a range of key analogues with partial structures to define the pharmacophore. Simplification of the caprazamycins was further pursued to develop diketopiperazine analogs.

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Synthetic approach toward antibiotic tunicamycins — VI total synthesis of tunicamycins

Cited by 40 publications

References 16 publications

A Modular Approach to the Total Synthesis of Tunicamycins

A Modular Approach to the Total Synthesis of Tunicamycins

Bacterial phosphoglycosyl transferases: initiators of glycan biosynthesis at the membrane interface

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

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