Stereoselective Synthesis of Ψ[CH 2 O] Pseudodipeptides and Conformational Analysis of a PheΨ[CH 2 O]Ala Containing Analogue of the Drug Desmopressin

Hedenström, Mattias; Holm, Lotta; Yuan, Zhong-Qing; Emtenäs, Hans; Kihlberg, Jan

doi:10.1016/s0960-894x(02)00016-1

Cited by 12 publications

(5 citation statements)

References 19 publications

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“…Furthermore, peptide mimetics based on polypyrrolinone scaffolds, mimicking the polyproline type II conformation of the native peptide ligands, as well as nonpeptidic small organic compounds have been reported to bind to class II MHC proteins. The Ile 260 −Ala 261 amide bond of CII260−267 has previously been replaced by a methylene ether isostere, which was found to decrease the binding affinity to the A q molecule while still allowing some T-cell hybridomas to recognize the A q /glycopeptide complex weakly. , …”

Section: Introductionmentioning

confidence: 99%

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

et al. 2007

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T cells obtained in a mouse model for rheumatoid arthritis are activated by a glycopeptide fragment from rat type II collagen (CII) bound to the class II major histocompatibility complex Aq molecule. We report a comparative model of Aq in complex with the glycopeptide CII260-267. This model was used in a structure-based design approach where the amide bond between Ala261 and Gly262 in the glycopeptide was selected for replacement with psi[COCH2], psi[CH2NH2+], and psi[(E)-CH=CH] isosteres. Ala-Gly isostere building blocks were then synthesized and introduced in CII260-267 and CII259-273 glycopeptides. The modified glycopeptides were evaluated for binding to the Aq molecule, and the results were interpreted in view of the Aq/glycopeptide model. Moreover, recognition by a panel of T-cell hybridomas revealed high sensitivity for the backbone modifications. These studies contribute to the understanding of the interactions in the ternary Aq/glycopeptide/T-cell receptor complexes that activate T cells in autoimmune arthritis and suggest possibilities for new vaccination approaches.

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Section: Introductionmentioning

confidence: 99%

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

et al. 2007

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“…When the amino alcohol derivative 11 was treated with PCC, the nitrile 12 was accessed in 62% yield, and the ester 13 was also obtained as a side product in 23% yield (entry 6). The simple β-hydroxy azide 14 underwent this transformation, providing the desired nitrile 15 . However, the isolated yield was not good (36%), mainly due to the formation of ester 16 (45%) (entry 7).…”

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confidence: 99%

New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Fan

et al. 2006

Org. Lett.

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“…The amino acids were reduced using LiAlH 4 and the resulting amino alcohols converted to the corresponding azides via treatment with TfN 3 . In this way, a variety of azides derived from various amino alcohols were obtained in good yields (70-76% yields) [ 24 , 25 , 26 , 27 , 28 , 29 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

et al. 2009

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A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

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Stereoselective Synthesis of Ψ[CH 2 O] Pseudodipeptides and Conformational Analysis of a PheΨ[CH 2 O]Ala Containing Analogue of the Drug Desmopressin

Cited by 12 publications

References 19 publications

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

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Stereoselective Synthesis of Ψ[CH 2 O] Pseudodipeptides and Conformational Analysis of a PheΨ[CH 2 O]Ala Containing Analogue of the Drug Desmopressin

Cited by 12 publications

References 19 publications

Probing Molecular Interactions within Class II MHC Aq/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

Probing Molecular Interactions within Class II MHC Aq/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

New One-Carbon Degradative Transformation of β-Alkyl-β-azido Alcohols

Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

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Product

Resources

About

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis

Probing Molecular Interactions within Class II MHC A^q/Glycopeptide/T-Cell Receptor Complexes Associated with Collagen-Induced Arthritis