Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Davies, Stephen G.; Garrido, Narciso M.; Kruchinin, Dennis; Ichihara, Osamu; Kotchie, Luke J.; Price, Paul D.; Mortimer, Anne J. Price; Russell, Angela J.; Smith, Andrew D.

doi:10.1016/j.tetasy.2006.05.008

Cited by 76 publications

(20 citation statements)

References 82 publications

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“…[6] In a retrosynthetic sense it was planned to synthesize 3 via the peptide acid 4 from acids 6-8, Fmoc-Ala-OH (9), and homoallylic alcohols 5 a-d (Scheme 1). [12] O-TIPSprotected (R)-Fmoc-b-tyrosine 6 was synthesized by a diastereoselective addition of (S)-N-benzyl-1-phenylethylamine [13] to the corresponding cinnamic acid benzyl ester followed by hydrogenolysis and Fmoc-introduction (Supporting Information). Ring-closing metathesis (RCM) as the key step could provide the 18-membered cyclodepsipeptide ring after esterification of the released peptide acid 4 with alcohols 5 a-d.…”

Section: Dedicated To Professor Reinhard W Hoffmann On the Ooccasionmentioning

confidence: 99%

Total Synthesis of Chondramide C and Its Binding Mode to F‐Actin

Waldmann

Renner

et al. 2008

Angew Chem Int Ed

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Actin glue: An E‐selective ring‐closing metathesis as the key step allowed the solid‐phase‐based total synthesis of the F‐actin stabilizer chondramide C as well as the establishment of its hitherto unknown stereochemistry. A strong influence of the polyketide configuration was revealed in cellular assays. Docking studies on the F‐actin filament structure led to a detailed model of the binding site.

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Section: Dedicated To Professor Reinhard W Hoffmann On the Ooccasionmentioning

confidence: 99%

Total Synthesis of Chondramide C and Its Binding Mode to F‐Actin

Waldmann

Renner

et al. 2008

Angew Chem Int Ed

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“…5 Therefore 2S,3S - and 2R,3R -DABA were chemically synthesized based on the published methods 6 (Figure S2) and tested in the ATP-[ 32 P]PP i exchange assay. As expected, PacP exhibited a preference toward reversible formation of 2S,3S -DABA-AMP; no substantial activation of 2R,3R -DABA was detected, validating the stereoselectivity of PacP (Figure 2a).…”

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confidence: 99%

Nine Enzymes Are Required for Assembly of the Pacidamycin Group of Peptidyl Nucleoside Antibiotics

et al. 2011

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Pacidamycins are a family of uridyl peptide antibiotics that inhibit the translocase MraY, an essential enzyme in bacterial cell wall biosynthesis not yet clinically targeted. The pacidamycin structural skeleton contains a doubly inverted peptidyl chain with a β-peptide and a ureido linkage, and a 3’-deoxyuridine nucleoside attached to DABA3 of the peptidyl chain via an enamide linkage. Although the biosynthetic gene cluster for pacidamycins was identified recently, the assembly line of this group of peptidyl nucleoside antibiotics remained poorly understood due to the highly dissociated nature of the encoded nonribosomal peptide synthetase (NRPS) domains and modules. In this work, a minimum set of enzymes were identified in generating the pacidamycin scaffold from amino acid and nucleoside monomers, highlighting a freestanding thiolation (T) domain (PacH) as a key carrier component in the peptidyl chain assembly, as well as a freestanding condensation (C) domain (PacI) catalyzing the release of the assembled peptide by a nucleoside moiety. Based on the substrate promiscuity of this enzymatic assembly line, several pacidamycin analogs were produced using in vitro total biosynthesis.

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“…( R )‐ 1 a (R 2 = t Bu): CAL‐A‐catalysed N‐acylation of rac ‐ 1 a yielded ( R )‐ 1 a ( ee >99 %) with [α] D 25 +19.6 ( c =1.00, CHCl 3 ). Literature value for ( S )‐ 1 a is −21.0 ( c =1.00, 20 °C, CHCl 3 ) and +20.0 ( c =0.71, 20 °C, CHCl 3 ) for ( R )‐ 1 a ( ee 99 %).…”

Section: Methodsmentioning

confidence: 98%

Acylation of β‐Amino Esters and Hydrolysis of β‐Amido Esters: Candida antarctica Lipase A as a Chemoselective Deprotection Catalyst

2016

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N‐Acylation by lipase A from Candida antarctica (CAL‐A) in ethyl butanoate was applied to the kinetic resolution of tert‐butyl esters of 3‐amino‐3‐phenylpropanoic acid (E>100), 3‐amino‐4‐methylpentanoic acid (E>100) and 3‐aminobutanoic acid (E=60) on 1.0–2.0 m scale. With the N‐acylated resolution products, the exceptional ability of CAL‐A to hydrolyse amides and bulky tert‐butyl esters was then studied. In all N‐acylated tert‐butyl esters, chemoselectivity favoured the amide bond cleavage. The tert‐butyl ester bond was left intact with 3‐amino‐3‐phenylpropanoate, whereas with 3‐amino‐4‐methylpentanoate and 3‐aminobutanoate the CAL‐A‐catalysed hydrolysis of tert‐butyl ester followed the amide hydrolysis.

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Homochiral lithium amides for the asymmetric synthesis of β-amino acids

Cited by 76 publications

References 82 publications

Total Synthesis of Chondramide C and Its Binding Mode to F‐Actin

Total Synthesis of Chondramide C and Its Binding Mode to F‐Actin

Nine Enzymes Are Required for Assembly of the Pacidamycin Group of Peptidyl Nucleoside Antibiotics

Acylation of β‐Amino Esters and Hydrolysis of β‐Amido Esters: Candida antarctica Lipase A as a Chemoselective Deprotection Catalyst

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