Absolute configuration of the .BETA.-hydroxyl fatty acid constituent of permetin A.

Murai, Asao; Amino, Yusuke; Ando, Toshihiko

doi:10.7164/antibiotics.38.1610

Cited by 18 publications

(14 citation statements)

References 7 publications

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“…The polypeptin class of cyclic cationic lipopeptides comprises the polypeptins [36][37][38] and pelgipeptins (Table III). 8,[39][40][41][42][43] They are nonapeptides with N-terminal acylation by a β-hydroxy fatty acid, whose hydroxyl moiety is linked to the C-terminal residue by an ester bond. The polypeptins and pelgipeptins show broad-spectrum activity against both Gram-positive and Gram-negative organisms, as well as some anaerobic bacteria.…”

Section: Polypeptinsmentioning

confidence: 99%

“…1). 8 In most but not all cases, lipopeptides are cyclized by an ester or amide linkage between a heteroatom on the side chain of an amino acid or lipid tail and the C-terminus, thereby restricting their conformations. Nonproteogenic amino acids are regularly incorporated into the peptide chain, and provide further diversity to this class of antibiotics.…”

Section: Introductionmentioning

confidence: 99%

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Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

Cochrane

Vederas

2014

Medicinal Research Reviews

371

320

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The emergence of multidrug-resistant bacteria has placed a strain on health care systems and highlighted the need for new classes of antibiotics. Bacterial lipopeptides are secondary metabolites, generally produced by nonribosomal peptide synthetases that often exhibit broad-spectrum antimicrobial activity. Only two new structural types of antibiotics have entered the market in the last 40 years, linezolid and the bacterial lipopeptide daptomycin. A wide variety of bacteria produce lipopeptides, however Bacillus and Paenibacillus spp. in particular have yielded several potent antimicrobial lipopeptides. Many of the lipopeptides produced by these bacteria have been known for decades and represent a potential gold mine of antibiotic candidates. This list includes the polymyxins, octapeptins, polypeptins, iturins, surfactins, fengycins, fusaricidins, and tridecaptins, as well as some novel examples, including the kurstakins. These lipopeptides have a wide variety of activities, ranging from antibacterial and antifungal, to anticancer and antiviral. This review presents a reasonably comprehensive list of each class of lipopeptide and their known homologues. Emphasis has been placed on their antimicrobial activities, as well other potential applications for this interesting class of substances.

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Section: Polypeptinsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

Cochrane

Vederas

2014

Medicinal Research Reviews

371

320

View full text Add to dashboard Cite

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“…l ‐isoleucine was converted into bis O ‐TBS protected derivative 20 in good yield . The subsequent treatment of 20 with oxalyl chloride in the presence of a catalytic amount of DMF afforded the corresponding acid chloride, which was condensed with 18 in pyridine to provide 21 in 92 % yield. The tert ‐butyl group was removed with TESOTf and 2,6‐lutidine to give 9 in 82 % yield …”

Section: Figurementioning

confidence: 99%

A Total Synthesis of Prunustatin A

et al. 2015

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At otal synthesis of prunustatin A, aG RP78 molecular chaperone down-regulator,h as been achieved. The key step in the synthesis is an intramolecular transesterification of the b-keto ester alcohol intermediate to construct the 15-membered tetralactone core of the natural product.Microbial species have the capability to produce aw ide variety of bioactive compounds with previously unknown structures and variousb iological activities. Prunustatin A( 1,F igure 1), a1 5-memberedt etralactone antibiotic with a3 -formamidosalicylic moiety first isolatedi n2 005 by Shin-ya and co-workers from as train of Streptomycesv iolaceoniger 4521-SVS3, showed inhibitory activity against GRP78 expression inducedb y2 -deoxyglucose stimulationi nH T1080 cells.[1] Subsequents tudies established that the tetralactone moiety is made up of four subunits,( 4 S)-2,2-dimethyl-4-hydroxy-3-oxo-5-phenylpentanoic acid, (S)-lactic acid, l-threonine, and (2S,3S)-2-hydroxy-3-methylpentanoic acid, as shown in Figure 1.[2] Prunustatin A( 1)i s similar in structure to SW-163A (2) [3] and neoantimycin (3). [4] neoantimycin (3)i sarare and unusualr ing-extended member of the antimycin class. The recent discoveryo f1 as as elective GRP78 molecular chaperone down-regulator,w hichc ould lead to the development of new approaches towards treating cancer,h ighlights the potential of this class as research probes.Antimycin A 3 ,o ne of the first knowna nd most potent inhibitors of the mitochondrial respiratory chain, binds to the quinone reduction site of the cytochrome bc 1 complex. Since UK-2A, an antimycin-class antibiotic, was first isolatedi n1 996 from as oil sample collecteda to ur campus by Shibata, Ta niguchi and co-workers, [5] we have been attempting to establish the structure-activity relationshipsa mong antimycin A 3 and UK-2A (Figure 2).[6] As an extension of our research, we have been engaged in studies towardt he synthesis and biological evaluation of 1.Herein, we report atotal synthesis of prunustatin A( 1).Our initial access to construct the tetralactone core of 1 was based on an intramolecular Mitsunobu reaction of 4 as previously reported (Scheme 1), [7] where we have developedt he CÀ Cb ond formation reactionb etween C1 and C11v ia Reformatsky reaction. However,a ll attempts at cyclizationsb etween O2 and C2 via intramolecular Mitsunobu reaction and other lactonization procedures resulted in the formation of undesired five-membered lactones.T his would be caused by the gem-dimethylg roups at C11.Recently,t he first total synthesis of 1 was reported, [8] where cyclized point was selected at O4 and C5 by conformational Scheme1.Our initial access to construct the tetralactone core of 1.Boc = tert-butyloxycarbonyl.[ analysisa nd molecular dynamics. With these results in mind, we embarkedo nanew synthetic strategy towards 1 that involved cyclization via transesterification of b-keto ester 8 followed by introduction of the gem-dimethyl groups at C11 (Scheme2). Conceptually,r ing-closure precursor 8 would be prepared by condensat...

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“…A methyl tetrahydropyran-2-yl acetate was obtained by refluxing its diazoketone precursor in methanol in the presence of silver (I) benzoate / triethylamine catalyst (Scheme 12, entry i) [49]. On the other hand, isoleucic acid homologs were obtained from the diazoketones at -40°C in MeOH (Scheme 12, entry ii) [50]. The rearrangement in water in the presence of Ag 2 O at ambient temperature gave statine analogues (Scheme 12, entry iii) [51,52].…”

Section: Scheme 11mentioning

confidence: 99%

Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids

Alberício¹

2008

COS

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Absolute configuration of the .BETA.-hydroxyl fatty acid constituent of permetin A.

Cited by 18 publications

References 7 publications

Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

A Total Synthesis of Prunustatin A

Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids

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Absolute configuration of the .BETA.-hydroxyl fatty acid constituent of permetin A.

Cited by 18 publications

References 7 publications

Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

Lipopeptides from Bacillus and Paenibacillus spp.: A Gold Mine of Antibiotic Candidates

A Total Synthesis of Prunustatin A

Asymmetric Synthesis of &#945;-Unsubstituted &#946;-Hydroxy Acids

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Asymmetric Synthesis of α-Unsubstituted β-Hydroxy Acids