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Light-mediated control of activity in a photosensitive foldamer that mimics an esterase.
Pollastrini M, Marafon G, Clayden J, Moretto A. Pollastrini M, et al. Chem Commun (Camb). 2021 Mar 2;57(18):2269-2272. doi: 10.1039/d0cc08309g. Chem Commun (Camb). 2021. PMID: 33533349
Photoisomerization of the fumaramide chromophore (with E geometry) to the corresponding maleamide (with Z geometry) brings together a 'catalytic triad' of Ser, His, and Asp, triggering esterase activity that is absent in the fumaramide isomer. The fumaramide/ …
Photoisomerization of the fumaramide chromophore (with E geometry) to the corresponding maleamide (with Z geometry) brings together a …
Gamma Radiation- and Ultraviolet-Induced Polymerization of Bis(amino acid)fumaramide Gel Assemblies.
Gregorić T, Makarević J, Štefanić Z, Žinić M, Frkanec L. Gregorić T, et al. Polymers (Basel). 2022 Jan 5;14(1):214. doi: 10.3390/polym14010214. Polymers (Basel). 2022. PMID: 35012236 Free PMC article.
Here, we report our investigation into the influences of self-assemblies of bis(amino acid vinyl ester)fumaramides on gamma-ray- and ultraviolet-induced polymerization. The gelator molecules self-assembled by non-covalent interactions, mainly through hydrogen bonds between …
Here, we report our investigation into the influences of self-assemblies of bis(amino acid vinyl ester)fumaramides on gamma-ray- and …
A Computational Study on the Reaction Mechanism of Stereocontrolled Synthesis of β-Lactam within [2]Rotaxane.
Liang R, Zhou Q, Li X, Wong MW, Chung LW. Liang R, et al. J Org Chem. 2023 Aug 4;88(15):10460-10469. doi: 10.1021/acs.joc.3c00330. Epub 2023 May 31. J Org Chem. 2023. PMID: 37257155
Our computational results suggest that the most favorable mechanism of the CsOH-promoted cyclization of the fumaramide into trans-beta-lactam within [2]rotaxane initiates with deprotonation of a N-benzyl group of the interlocked fumaramide substrate by CsOH, followe …
Our computational results suggest that the most favorable mechanism of the CsOH-promoted cyclization of the fumaramide into trans-bet …
Control of the assembly of a cyclic hetero[4]pseudorotaxane from a self-complementary [2]rotaxane.
Saura-Sanmartin A, Nicolas-Garcia T, Pastor A, Quiñonero D, Alajarin M, Martinez-Cuezva A, Berna J. Saura-Sanmartin A, et al. Chem Sci. 2023 Mar 22;14(15):4143-4151. doi: 10.1039/d3sc00886j. eCollection 2023 Apr 12. Chem Sci. 2023. PMID: 37063802 Free PMC article.
The disassembly of the cyclic dimer was also achieved through a Diels-Alder reaction over the fumaramide binding site of the thread, triggering the translational motion of the entwined macrocycle to an adjacent glycylglycine-based station and precluding the supramolecular …
The disassembly of the cyclic dimer was also achieved through a Diels-Alder reaction over the fumaramide binding site of the thread, …
Helical Foldamers Incorporating Photoswitchable Residues for Light-Mediated Modulation of Conformational Preference.
Mazzier D, Crisma M, De Poli M, Marafon G, Peggion C, Clayden J, Moretto A. Mazzier D, et al. J Am Chem Soc. 2016 Jun 29;138(25):8007-18. doi: 10.1021/jacs.6b04435. Epub 2016 Jun 16. J Am Chem Soc. 2016. PMID: 27258674
An E unsaturated fumaramide linkage may be introduced into Aib peptide foldamer structures by standard coupling methods and photoisomerized to its Z (maleamide) isomer by irradiation with UV light. As a result of the photoisomerization, a new hydrogen-bonded contact become …
An E unsaturated fumaramide linkage may be introduced into Aib peptide foldamer structures by standard coupling methods and photoisom …
Ring-to-Thread Chirality Transfer in [2]Rotaxanes for the Synthesis of Enantioenriched Lactams.
Lopez-Leonardo C, Saura-Sanmartin A, Marin-Luna M, Alajarin M, Martinez-Cuezva A, Berna J. Lopez-Leonardo C, et al. Angew Chem Int Ed Engl. 2022 Sep 26;61(39):e202209904. doi: 10.1002/anie.202209904. Epub 2022 Aug 19. Angew Chem Int Ed Engl. 2022. PMID: 35916122 Free PMC article.
Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, and nonsymmetric N-(arylmethyl)fumaramides as the axis. The base-promoted cyclization of the initial fumaramide thread allows …
Herein we describe the synthesis of orientational mechanostereoisomers, which include a benzylic amide macrocycle with a stereogenic center, …
Anion Selective Ion Channel Constructed from a Self-Assembly of Bis(cholate)-Substituted Fumaramide.
Malla JA, Roy A, Talukdar P. Malla JA, et al. Org Lett. 2018 Oct 5;20(19):5991-5994. doi: 10.1021/acs.orglett.8b02115. Epub 2018 Sep 27. Org Lett. 2018. PMID: 30260230
The self-assembled ion channel constructed from bis(cholate)-substituted fumaramide is reported. Such ion channel formation was favored by intermolecular hydrogen bonding interactions among fumaramide moieties. ...Theoretical calculations were done to confirm the hy …
The self-assembled ion channel constructed from bis(cholate)-substituted fumaramide is reported. Such ion channel formation was favor …
Adsorption of fumaramide [2]rotaxane and its components on a solid substrate: a coverage-dependent study.
Whelan CM, Gatti F, Leigh DA, Rapino S, Zerbetto F, Rudolf P. Whelan CM, et al. J Phys Chem B. 2006 Aug 31;110(34):17076-81. doi: 10.1021/jp061836c. J Phys Chem B. 2006. PMID: 16928002
The coverage-dependent adsorption on Au(111) of a fumaramide [2]rotaxane and its components, a benzylic amide macrocycle and a fumaramide thread, is studied using high-resolution electron energy loss spectroscopy (HREELS). ...
The coverage-dependent adsorption on Au(111) of a fumaramide [2]rotaxane and its components, a benzylic amide macrocycle and a fum …
Homo and heteroassembly of amide-based [2]rotaxanes using α,α'-dimethyl-p-xylylenediamines.
Lopez-Leonardo C , Martinez-Cuezva A , Bautista D , Alajarin M , Berna J . Lopez-Leonardo C , et al. Chem Commun (Camb). 2019 Jun 6;55(47):6787-6790. doi: 10.1039/c9cc02701g. Chem Commun (Camb). 2019. PMID: 31120080
The formation of [2]rotaxanes via a fumaramide-templated clipping reaction using alpha,alpha'-dimethyl-p-xylylenediamines is described. ...
The formation of [2]rotaxanes via a fumaramide-templated clipping reaction using alpha,alpha'-dimethyl-p-xylylenediamines is describe …
Two new beta-strand mimics.
Tsai JH, Waldman AS, Nowick JS. Tsai JH, et al. Bioorg Med Chem. 1999 Jan;7(1):29-38. doi: 10.1016/s0968-0896(98)00225-9. Bioorg Med Chem. 1999. PMID: 10199654
Beta-strand mimic B is composed of a 5-amino-2-methoxybenzoic acid unit linked by a diacylhydrazine group to a fumaramide unit; beta-strand mimic C is composed of a 5-amino-2-methoxybenzoic acid unit linked by a diacylhydrazine group to a peptide. ...
Beta-strand mimic B is composed of a 5-amino-2-methoxybenzoic acid unit linked by a diacylhydrazine group to a fumaramide unit; beta- …
41 results