Synthesis of the diazepanone-nucleoside portion of liposidomycins by aldol reaction of the enolate of diazepanone with a nucleoside 5′-aldehyde

Kim, Kwan Soo; Ahn, Yeong Hee

doi:10.1016/s0957-4166(98)00366-8

Cited by 25 publications

(6 citation statements)

References 13 publications

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“…Construction of the syn ‐β‐hydroxy amino acid moiety with an S configuration at C5′ was then investigated. Several strategies have been employed for this in the past,5d,e, 6g,i–k, 7a, 8a two of which were used for the total synthesis of caprazol. One is a Sharpless asymmetric aminohydroxylation of the α,β‐unsaturated ester7a and the other is the diastereoselective isocyanoacetate aldol reaction 8a.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of (−)‐Caprazamycin A

et al. 2015

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Caprazamycin A has significant antibacterial activity against Mycobacterium tuberculosis (TB). The first total synthesis is herein reported and features a) the scalable preparation of the syn‐β‐hydroxy amino acid with a thiourea‐catalyzed diastereoselective aldol reaction, b) construction of a diazepanone with an unstable fatty‐acid side chain, and c) global deprotection with hydrogenation. This report provides a route for the synthesis of related liponucleoside antibiotics with fatty‐acid side chains.

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Section: Methodsmentioning

confidence: 99%

Total Synthesis of (−)‐Caprazamycin A

et al. 2015

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“…The central diazepanone ring in caprazamycin (14, Figure 4) plays a critical anchoring role, orienting the other subunits and facilitating their highly specific interactions within MraY's active site [47]. As the diazepanone ring adds further complexity to synthesis however [48][49][50][51][52][53][54][55], its isosteric substitution with both cyclic and acyclic, or complete removal, are being investigated for use as diazepanone substitutes. 3) [56].…”

Section: Modifications On Diazepanone Ring (Subunit C)mentioning

confidence: 99%

Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY

Patel

Ryan

Makwana

et al. 2019

European Journal of Medicinal Chemistry

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The present status of antibiotic resistant requires an urgent invention of novel agents that act on clinically unexplored antibacterial targets. The enzyme MraY (phospho-MurNAcpentapeptide translocase), essential for bacterial cell wall synthesis, fulfils this criterion as it has not been explored as a target in a clinical context. Specifically, the enzyme is involved in the lipidlinked cycle of peptidoglycan biosynthesis and is reportedly targeted by naturally-occurring nucleoside antibiotics. The antimicrobial 'caprazamycin' class of nucleoside antibiotics targets Mycobacterium tuberculosis and clinically relevant Gram-negative bacteria such as Pseudomonas aeruginosa besides various drug resistant strains and is therefore an eligible starting point for the development of novel agents. In this review, we aim to summarise the structure-activity relationships of the natural, semi-synthetic as well as synthetic analogues of nucleoside antibiotic caprazamycins. This review highlights caprazamycins as promising lead structures for development of potent and selective antimicrobial agents that target MraY, the bacterial enzyme involved in the first membrane-dependent step in bacterial peptidoglycan assembly.

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“…More than 8 groups have studied the total synthesis of LPMs. [123][124][125][126][127][128][129][130][131][132][133][134][135][136][137][138][139][140] Difficulty in the synthesis of this class of molecules may lie with the introduction of 5-aminoribose moiety found in CPZs and LPMs after construction of a uridyldiazepanone moiety because the tertiary amine contained in the diazepanone structure inhibited the usual ribosylation promoted by Lewis acid. In addition, CPZs and LPMs would be sensitive to basic conditions because they contain a b-heterosubstituted carboxyl moiety.…”

Section: -110)mentioning

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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Synthesis of the diazepanone-nucleoside portion of liposidomycins by aldol reaction of the enolate of diazepanone with a nucleoside 5′-aldehyde

Cited by 25 publications

References 13 publications

Total Synthesis of (−)‐Caprazamycin A

Total Synthesis of (−)‐Caprazamycin A

Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY

Fine Synthetic Nucleoside Chemistry Based on Nucleoside Natural Products Synthesis

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