Synthesis of the Oligosaccharide Moieties of Musettamycin, Marcellomycin and Aclacinomycin A, Antitumor Antibiotics

Monneret, Claude; Martin, Alain; Païs, M.

doi:10.1080/07328308808058934

Cited by 9 publications

(4 citation statements)

References 18 publications

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“…This includes the use of silver zeolites 65 and mercuric salts (Helferich conditions). 66 , 67 These approaches have not been as widely used with deoxy-sugars as they have with their fully substituted counterparts.…”

Section: Direct Synthesismentioning

confidence: 99%

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Methods for 2-Deoxyglycoside Synthesis

2018

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Deoxy-sugars often play a critical role in modulating the potency of many bioactive natural products. Accordingly, there has been sustained interest in methods for their synthesis over the past several decades. The focus of much of this work has been on developing new glycosylation reactions that permit the mild and selective construction of deoxyglycosides. This Review covers classical approaches to deoxyglycoside synthesis, as well as more recently developed chemistry that aims to control the selectivity of the reaction through rational design of the promoter. Where relevant, the application of this chemistry to natural product synthesis will also be described.

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Section: Direct Synthesismentioning

confidence: 99%

“…In addition to these examples, other heavy metal promoters have been used to activate deoxy-sugar bromides. This includes the use of silver zeolites and mercuric salts (Helferich conditions). , These approaches have not been as widely used with deoxy-sugars as they have with their fully substituted counterparts.…”

Section: Direct Synthesismentioning

confidence: 99%

Methods for 2-Deoxyglycoside Synthesis

2018

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“…Several years ago, we reported the synthesis of the trisaccharide of ciclamycin 0 using the sulfoxide glycosylation reaction. , Our synthesis of the trisaccharide used a polymerization reaction in which the trisaccharide was constructed in a single reaction from three monomers, 4a , 5a , and 6 (see Scheme ) . The reactivities of the sulfoxides and nucleophiles were tuned such that the linkage between the A ring and B ring would occur first, followed by formation of the linkage to the C ring.…”

Section: Introductionmentioning

confidence: 99%

Scavenging Byproducts in the Sulfoxide Glycosylation Reaction: Application to the Synthesis of Ciclamycin 0

et al. 1999

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We have developed a direct and efficient route for the synthesis of ciclamycin 0 using the sulfoxide glycosylation reaction to form the glycosidic linkages. In the course of completing the synthesis of ciclamycin 0, we developed new glycosylation conditions that improve the outcome of the sulfoxide reaction. The conditions involve the addition of agents that scavenge phenylsulfenyl triflate, a highly reactive byproduct that forms following activation of anomeric sulfoxides with triflic anhydride.

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“…In previously reported synthesis, Diels–Alder reactions were found to be crucial for the synthesis of aklavinone, which raised the issue of regioselectivity [ 22 , 23 ]. It was reported that refinement led to only a 68% yield ratio of oligosaccharides in ACM-A [ 24 , 25 ]. Clearly, high stereoselectivity is desired, but the modulation of stereoselectivity is laborious and troublesome [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Rethinking Biosynthesis of Aclacinomycin A

Tian

2023

Molecules

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Aclacinomycin A (ACM-A) is an anthracycline antitumor agent widely used in clinical practice. The current industrial production of ACM-A relies primarily on chemical synthesis and microbial fermentation. However, chemical synthesis involves multiple reactions which give rise to high production costs and environmental pollution. Microbial fermentation is a sustainable strategy, yet the current fermentation yield is too low to satisfy market demand. Hence, strain improvement is highly desirable, and tremendous endeavors have been made to decipher biosynthesis pathways and modify key enzymes. In this review, we comprehensively describe the reported biosynthesis pathways, key enzymes, and, especially, catalytic mechanisms. In addition, we come up with strategies to uncover unknown enzymes and improve the activities of rate-limiting enzymes. Overall, this review aims to provide valuable insights for complete biosynthesis of ACM-A.

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Synthesis of the Oligosaccharide Moieties of Musettamycin, Marcellomycin and Aclacinomycin A, Antitumor Antibiotics

Cited by 9 publications

References 18 publications

Methods for 2-Deoxyglycoside Synthesis

Methods for 2-Deoxyglycoside Synthesis

Scavenging Byproducts in the Sulfoxide Glycosylation Reaction: Application to the Synthesis of Ciclamycin 0

Rethinking Biosynthesis of Aclacinomycin A

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