Some Selective Reactions of Moenomycin A

Vogel, Stefan; Buchynskyy, Andrij; Stembera, Katka; Richter, Karin; Hennig, Lothar; Müller, D.; Welzel, Peter; Maquin, F.; Bonhomme, Christian; Lampilas, Maxime

doi:10.1016/s0960-894x(00)00377-2

Cited by 28 publications

(17 citation statements)

References 11 publications

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“…We have shown previously that removal of the carbamoyl group from moenomycin to give 1 b is accompanied by the loss of antibiotic activity. [32] In keeping with this, 1 b showed a markedly reduced affinity for PBP 1b (B 50 5 Â 10 À4 M) in the SPR elution experiments when compared to moenomycin A (1 a). On the other hand removal of the chromophore part from 1 a to give 1 c is neither of consequence for the antibiotic activity nor for binding to the enzyme preparation (see Table 1).…”

Section: Spr Competition Experimentssupporting

confidence: 64%

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A Surface Plasmon Resonance Analysis of the Interaction between the Antibiotic Moenomycin A and Penicillin‐Binding Protein 1b

et al. 2002

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The antibiotic moenomycin A inhibits the biosynthesis of peptidoglycan, the main structural polymer of the bacterial cell wall. The inhibition is based on a reversible binding of the antibiotic to one of the substrate binding sites in enzymes such as penicillin-binding protein (PBP) 1b. A novel assay based on surface plasmon resonance (SPR) has been established that can be used to investigate selective binding of the moenomycin sugar moiety and other transglycosylase inhibitors to this enzyme. Suitable ligands were prepared from moenomycin A and coupled to SPR sensor surfaces. Moenomycin analogues with structural variations were used to perform competitive SPR experiments with PBP 1b. The SPR results confirm for the first time that the trisaccharide fragment of moenomycin A (C-E-F-G-H-I) is the minimal structure that possesses all moieties sufficient for biological activity and for affinity towards PBP 1b. The method seems to be appropriate for use in screens for transglycosylase inhibitors that bind to the moenomycin-binding site of the enzyme.

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Section: Spr Competition Experimentssupporting

confidence: 64%

“…Decarbamoyl moenomycin (1 b) [32] and derivative 1 c [33] provided a nice confirmation of the reliability of the method. We have shown previously that removal of the carbamoyl group from moenomycin to give 1 b is accompanied by the loss of antibiotic activity.…”

Section: Spr Competition Experimentsmentioning

confidence: 67%

A Surface Plasmon Resonance Analysis of the Interaction between the Antibiotic Moenomycin A and Penicillin‐Binding Protein 1b

et al. 2002

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“…trisaccharides 24-29 , 31 and their pentasaccharide precursors,61 several other approaches were developed to replace moenocinol with various functional groups (Scheme 2). Ozonolysis in methanolic solution of 1 afforded aldehyde 46 , lacking lipid and chromophore units, which was easily converted to primary alcohol 47 93. Different analogs with modified lipid chains were obtained either through indium-mediated Barbier-type reactions of 46 with allylic and benzylic halides (for example, 48-50 ),94 or reductive aminations of 46 (compounds 51-54 ) 95…”

Section: Moenomycins As a Target Of Chemical Synthesis And Degradatmentioning

confidence: 99%

Moenomycin family antibiotics: chemical synthesis, biosynthesis, and biological activity

2010

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The review (with 214 references cited) is devoted to moenomycins, the only known group of antibiotics that directly inhibit bacterial peptidoglycan glycosytransferases. Naturally occurring moenomycins and chemical and biological approaches to their derivatives are described. The biological properties of moenomycins and plausible mechanisms of bacterial resistance to them are also covered here, portraying a complete picture of the chemistry and biology of these fascinating natural products

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“…The three-dimensional structure of the phosphoglycolipid moenomycin ( Fig. 35.6), which is employed as a growth promoter in animal nutrition, has been determined [46] and extensive SAR studies have been carried out [47,48]. Analogues that contain at least three sugar units (C, E, F) and the phospholipid are active in vivo against Gram-positive bacteria.…”

Section: Peptidoglycanmentioning

confidence: 99%

Carbohydrate‐Based Drug Discovery in the Battle against Bacterial Infections: New Opportunities Arising from Programmable One‐Pot Oligosaccharide Synthesis

Ritter¹,

Wong

2003

Carbohydrate‐Based Drug Discovery

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Some Selective Reactions of Moenomycin A

Cited by 28 publications

References 11 publications

A Surface Plasmon Resonance Analysis of the Interaction between the Antibiotic Moenomycin A and Penicillin‐Binding Protein 1b

A Surface Plasmon Resonance Analysis of the Interaction between the Antibiotic Moenomycin A and Penicillin‐Binding Protein 1b

Moenomycin family antibiotics: chemical synthesis, biosynthesis, and biological activity

Carbohydrate‐Based Drug Discovery in the Battle against Bacterial Infections: New Opportunities Arising from Programmable One‐Pot Oligosaccharide Synthesis

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