A New Strategy To Produce β-Peptides:  Use of Alicyclic β-Lactams

Fülöp, Ferenc; Forró, Enikő; Tóth, Gábor

doi:10.1021/ol048356t

Cited by 21 publications

(4 citation statements)

References 47 publications

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“…Finally, isolation of tetrapeptide 437 was achieved in the conditions shown in Scheme . The HPLC analysis indicated that no epimerization occurred during the synthesis …”

Section: Synthesis Of Amino(hydroxy) Acid Derivativesmentioning

confidence: 99%

β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products

2007

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“…Finally, isolation of tetrapeptide 437 was achieved in the conditions shown in Scheme . The HPLC analysis indicated that no epimerization occurred during the synthesis …”

Section: Synthesis Of Amino(hydroxy) Acid Derivativesmentioning

confidence: 99%

β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products

2007

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“…Compound (±)-4, our next selected substrate, was obtained by N-Boc protection of lactam (±)-1. Modification of the reported procedure [28] resulted in an increased product yield of this step. ROM of compound (±)-4 was performed analogously to ring opening of (±)-1.…”

Section: Scheme 1 Cross-metathesis Of Lactam (±)-2 With Fluorinated mentioning

confidence: 99%

Stereocontrolled synthesis of fluorine-containing functionalized β-lactam derivatives through cross-metathesis reactions

Kiss¹

2019

FNotes

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Functionalized β-lactams and their derivatives have generated increasing interest in medicinal chemistry over the last decades. Because of their pharmacological potential the chemistry of fluorinated β-lactams and β-amino acids is considered to be an expanding research field. The stereocontrolled synthesis of various fluorine-containing acylic β-lactams has been accomplished from some readily available unsaturated bicyclic β-lactam isomers. The synthetic strategy was based on ring-opening metathesis of unsaturated bicyclic azetidinones followed by cross-metathesis with fluorine-containing olefins. The cross-metathesis transformations, performed under various conditions with the aim of studying chemodiscrimination of the olefin bonds, resulted in the corresponding functionalized β-lactam derivatives.

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“…Academic groups have also shown considerable interest in the conformational changes resulting from incorporation of β‐amino acids into peptides 7–10. In addition, β‐peptides frequently exhibit retarded metabolism and are more resistant to protease enzymes.…”

Section: Introductionmentioning

confidence: 99%

A concise synthesis of single‐enantiomer β‐lactams and β‐amino acids using Rhodococcus globerulus

Lloyd¹,

Lloyd²,

Keene³

et al. 2007

J of Chemical Tech & Biotech

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BACKGROUND: Pharmaceutical companies continue to evaluate β-amino acids and β-lactams in a range of drug candidates. The development of a highly efficient and selective bioresolution of cyclic β-lactam substrates could yield enantiopure lactams and β-amino acids with medicinal potential. The aim of this work was to discover and develop a biocatalyst capable of selectively hydrolysing β-lactam substrates.

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A New Strategy To Produce β-Peptides: Use of Alicyclic β-Lactams

Cited by 21 publications

References 47 publications

β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products

β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products

Stereocontrolled synthesis of fluorine-containing functionalized β-lactam derivatives through cross-metathesis reactions

A concise synthesis of single‐enantiomer β‐lactams and β‐amino acids using Rhodococcus globerulus

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