Synthesis of Highly Functionalized Fluorinated Cispentacin Derivatives

Fluorinated highly functionalized cispentacin derivatives were synthetised starting from an unsaturated bicyclic β‐lactam through CC bond functionalization via the dipolar cycloaddition of a nitrile oxide, isoxazoline opening, and fluorination by OH/F exchange.

[1]  V. Soloshonok,et al.  Recent Advances in the Asymmetric Synthesis of α-(Trifluoromethyl)-Containing α-Amino Acids , 2012 .

[2]  B. Koksch,et al.  Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions. , 2012, Chemical Society reviews.

[3]  O. Illa,et al.  Designing hybrid foldamers: the effect on the peptide conformational bias of β- versus α- and γ-linear residues in alternation with (1R,2S)-2-aminocyclobutane-1-carboxylic acid. , 2012, Organic & biomolecular chemistry.

[4]  M. Doddareddy,et al.  The enantiomers of syn-2,3-difluoro-4-aminobutyric acid elicit opposite responses at the GABA(C) receptor. , 2012, Chemical communications.

[5]  F. Fülöp,et al.  Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines , 2012, Beilstein journal of organic chemistry.

[6]  F. Fülöp,et al.  Peptidic foldamers: ramping up diversity. , 2012, Chemical Society reviews.

[7]  P. R. Rajamohanan,et al.  Synthesis and structural characterization of homochiral homo-oligomers of parent cis- and trans-furanoid-β-amino acids. , 2011, Chemistry.

[8]  F. Fülöp,et al.  Regio- and diastereoselective fluorination of alicyclic β-amino acids. , 2011, Organic & biomolecular chemistry.

[9]  F. Fülöp,et al.  Selective Synthesis of New Fluorinated Alicyclic β‐Amino Ester Stereoisomers , 2011 .

[10]  F. Fülöp,et al.  Synthesis of novel isoxazoline-fused cyclic β-amino esters by regio- and stereo-selective 1,3-dipolar cycloaddition , 2011 .

[11]  D. Amabilino,et al.  Self-assembly of chiral trans-cyclobutane-containing β-dipeptides into ordered aggregates. , 2011, Chemistry.

[12]  I. Komarov,et al.  Synthesis of β-fluoro-β-proline , 2011 .

[13]  Thomas S. Peat,et al.  Structural and Functional Basis of Resistance to Neuraminidase Inhibitors of Influenza B Viruses† , 2010, Journal of medicinal chemistry.

[14]  R. Guillot,et al.  12-Helix folding of cyclobutane beta-amino acid oligomers. , 2010, Organic letters.

[15]  J. L. Aceña,et al.  Recent Developments in the Synthesis of Fluorinated -Amino Acids , 2010 .

[16]  V. Soloshonok,et al.  Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group , 2010 .

[17]  Choon‐Hong Tan,et al.  Enantioselective synthesis of alpha-fluorinated beta-amino acid derivatives by an asymmetric mannich reaction and selective deacylation/decarboxylation reactions. , 2010, Chemistry.

[18]  M. Luo,et al.  Development of new stereodiverse diaminocyclitols as inhibitors of influenza virus neuraminidase. , 2010, Organic letters.

[19]  V. Branchadell,et al.  Synthesis and structural study of novel dimethylcyclobutyl β-peptides , 2009 .

[20]  F. Avilés,et al.  Cyclobutane-containing peptides: evaluation as novel metallocarboxypeptidase inhibitors and modelling of their mode of action. , 2009, Bioorganic & medicinal chemistry.

[21]  F. Fülöp,et al.  Synthesis of novel isoxazoline-fused cispentacin stereoisomers , 2009 .

[22]  D. Aitken,et al.  Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form. , 2009, The Journal of organic chemistry.

[23]  C. del Pozo,et al.  Cross-metathesis reactions as an efficient tool in the synthesis of fluorinated cyclic beta-amino acids. , 2009, The Journal of organic chemistry.

[24]  D. Seebach,et al.  Enantioselective Preparation of ߲-Amino Acid Derivatives for -Peptide Synthesis , 2009 .

[25]  D. Seebach,et al.  Electrophilic S‐Trifluoromethylation of Cysteine Side Chains in α‐ and β‐Peptides: Isolation of Trifluoro‐methylated Sandostatin® (Octreotide) Derivatives , 2008 .

[26]  B. Koksch,et al.  Synthetic strategies to alpha-trifluoromethyl and alpha-difluoromethyl substituted alpha-amino acids. , 2008, Chemical Society reviews.

[27]  Valerio D’Elia,et al.  Short alpha/beta-peptides as catalysts for intra- and intermolecular aldol reactions. , 2008, The Journal of organic chemistry.

[28]  X. Y. Zhang,et al.  QSAR study of neuraminidase inhibitors based on heuristic method and radial basis function network. , 2008, European journal of medicinal chemistry.

[29]  G. Sheldrick.  A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[30]  B. Jaun,et al.  NMR‐Solution Structures of Fluoro‐Substituted β‐Peptides: A 314‐Helix and a Hairpin Turn. The First Case of a 90° OCCF Dihedral Angle in an α‐Fluoro‐Amide Group , 2007 .

[31]  E. Giralt,et al.  Self-Assembly of a Cyclobutane β-Tetrapeptide To Form Nanosized Structures , 2007 .

[32]  M. Roje,et al.  Quinine-mediated parallel kinetic resolution of racemic cyclic anhydride: stereoselective synthesis, relative and absolute configuration of novel alicyclic β-amino acids , 2007 .

[33]  C. del Pozo,et al.  Asymmetric synthesis of fluorinated cyclic beta-amino acid derivatives through cross metathesis. , 2006, Organic letters.

[34]  D. Aitken,et al.  A solution to the component instability problem in the preparation of peptides containing C2-substituted cis-cyclobutane β-aminoacids: synthesis of a stable rhodopeptin analogue , 2006 .

[35]  F. Fülöp,et al.  Application of alicyclic β-amino acids in peptide chemistry , 2006 .

[36]  Pooran Chand,et al.  Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo. , 2005, Bioorganic & medicinal chemistry.

[37]  F. Qing,et al.  Synthesis of fluorinated amino acids , 2004 .

[38]  P. Kast,et al.  Probing the Proteolytic Stability of β‐Peptides Containing α‐Fluoro‐ and α‐Hydroxy‐β‐Amino Acids , 2004 .

[39]  W. Seufert,et al.  Evaluation of the Molecular Interactions of Fluorinated Amino Acids with Native Polypeptides , 2004, Chembiochem : a European journal of chemical biology.

[40]  María Sánchez-Roselló,et al.  New approaches to the synthesis of organofluorine nitrogenated derivatives , 2004 .

[41]  Ali Dehghani,et al.  Syntheses and neuraminidase inhibitory activity of multisubstituted cyclopentane amide derivatives. , 2004, Journal of medicinal chemistry.

[42]  Ferenc Fülöp,et al.  Side-chain control of beta-peptide secondary structures. , 2003, European journal of biochemistry.

[43]  Zongru Guo,et al.  Study on molecular mechanism and 3D-QSAR of influenza neuraminidase inhibitors. , 2003, Bioorganic & medicinal chemistry.

[44]  Hans-Christian Militzer,et al.  Novel antifungal β-amino acids: synthesis and activity against Candida albicans , 2003 .

[45]  Krishna Kumar,et al.  Fluorinated amino acids in protein design and engineering. , 2002, Chemical Society reviews.

[46]  A J Elliott,et al.  Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity. , 2001, Journal of medicinal chemistry.

[47]  F. Fülöp,et al.  The chemistry of 2-aminocycloalkanecarboxylic acids. , 2001, Chemical reviews.

[48]  C. Willis,et al.  Synthesis of fluorinated amino acids. , 2004, Natural product reports.

[49]  D. Seebach,et al.  Preparation of Achiral and of Enantiopure Geminally Disubstituted β‐Amino Acids for β‐Peptide Synthesis , 2000 .

[50]  Maria Cristina Burla,et al.  SIR97: a new tool for crystal structure determination and refinement , 1999 .

[51]  D. Seebach,et al.  Nonreductive Enantioselective Ring Opening of N‐(Methylsulfonyl)dicarboximides with Diisopropoxytitanium α,α,α′,α′‐Tetraaryl‐1,3‐dioxolane‐4,5‐dimethanolate , 1996 .

[52]  J. S. Reid,et al.  The Analytical Calculation of Absorption in Multifaceted Crystals , 1995 .