[NMR paper] A few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives.
A few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives.
Related ArticlesA few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives.
Eur J Med Chem. 2015 Apr 13;94:73-86
Authors: Bereczki I, Mándi A, R?th E, Borbás A, Fizil Á, Komáromi I, Sipos A, Kurtán T, Batta G, Ostorházi E, Rozgonyi F, Vanderlinden E, Naesens L, Sztaricskai F, Herczegh P
Abstract
Despite the close structural similarity between the heptapeptide cores of the glycopeptide antibiotics teicoplanin and ristocetin, synthetically modified derivatives of their aglycons show significantly different antibacterial and antiviral properties. The teicoplanin aglycon derivatives with one exception proved to be potent antibacterials but they did not exhibit anti-influenza virus activity. In contrast, the aglycoristocetin derivatives generally showed high anti-influenza virus activity and possessed moderate antibacterial activity. A systematic structure-activity relationship study has been carried out on ristocetin and teicoplanin aglycon derivatives, to explore which structural differences are responsible for these markedly different biological activities. According to electronic circular dichroism and in silico conformational studies, it was found that the differences in anti-influenza virus activity are mainly determined by the conformation of the heptapeptide core of the antibiotics controlled by the presence or absence of chloro substituents. Knowledge of the bioactive conformation will help to design new analogs with improved anti-influenza virus activity. For the teicoplanin derivatives, it was shown that derivatization to improve the antiviral efficacy was accompanied by a significant decrease in antibacterial activity.
[NMR paper] Antiviral Atropisomers: Conformational Energy Surfaces by NMR for Host-Directed Myxovirus Blockers.
Antiviral Atropisomers: Conformational Energy Surfaces by NMR for Host-Directed Myxovirus Blockers.
Antiviral Atropisomers: Conformational Energy Surfaces by NMR for Host-Directed Myxovirus Blockers.
J Chem Inf Model. 2014 Jul 24;
Authors: Grimmer C, Moore TW, Padwa A, Prussia A, Wells G, Wu S, Sun A, Snyder JP
Abstract
Biologically active organic molecules characterized by a high single bond torsional barrier generate isolable isomers (atropisomers) and offer a unique stereochemical component to the design of selective...
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[NMR paper] Atomic mapping of the interactions between the antiviral agent cyanovirin-N and oligo
Atomic mapping of the interactions between the antiviral agent cyanovirin-N and oligomannosides by saturation-transfer difference NMR.
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Biochemistry. 2004 Nov 9;43(44):13926-31
Authors: Sandström C, Berteau O, Gemma E, Oscarson S, Kenne L, Gronenborn AM
The minimum oligosaccharide structure required for binding to the potent HIV-inactivating protein cyanovirin-N (CV-N) was determined by...
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[NMR paper] NMR difference spectroscopy with a dual saddle-coil difference probe.
NMR difference spectroscopy with a dual saddle-coil difference probe.
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Anal Bioanal Chem. 2004 Mar;378(6):1520-7
Authors: Macnaughtan MA, Smith AP, Goldsbrough PB, Santini RE, Raftery D
A new difference probe for nuclear magnetic resonance (NMR) spectroscopy is presented. The difference probe uses two saddle-shaped coils to excite and detect two samples simultaneously. The samples are held in a specially modified 3-mm NMR tube with an Ultem plastic disk to...
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[NMR paper] 1H NMR studies on the interaction of beta-carboline derivatives with human serum albu
1H NMR studies on the interaction of beta-carboline derivatives with human serum albumin.
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J Magn Reson. 1998 Feb;130(2):281-6
Authors: Veglia G, Delfini M, Giudice MR, Gaggelli E, Valensin G
1H NMR studies were performed on two beta-carboline derivatives interacting with human serum albumin. The spin-lattice relaxation rates of the two derivatives, having side chains of different length and polarity, were used to demonstrate a diverse...
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[NMR paper] The solution structure of the synthetic circular peptide CGVSRQGKPYC. NMR studies of
The solution structure of the synthetic circular peptide CGVSRQGKPYC. NMR studies of the folding of a synthetic model for the DNA-binding loop of the ssDNA-binding protein encoded by gene V of phage M13.
http://www.ncbi.nlm.nih.gov/corehtml/query/egifs/http:--www3.interscience.wiley.com-aboutus-images-wiley_interscience_pubmed_logo_FREE_120x27.gif Related Articles The solution structure of the synthetic circular peptide CGVSRQGKPYC. NMR studies of the folding of a synthetic model for the DNA-binding loop of the ssDNA-binding protein encoded by gene V of phage M13.
Eur...
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[NMR paper] NMR and CD studies on the conformation of a synthetic peptide containing epitopes of
NMR and CD studies on the conformation of a synthetic peptide containing epitopes of the human immunodeficiency virus 1 transmembrane protein gp41.
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Biopolymers. 1996 Mar;38(3):423-35
Authors: Consonni R, Limiroli R, Longhi R, Manera E, Vecchio G, Ragona L, Siccardi AG, Zetta L
CD and nmr characterizations are reported for the 23-mer peptide CMC3, corresponding to residues 577-599...
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[NMR paper] NMR and circular dichroism studies of synthetic peptides derived from the third intra
NMR and circular dichroism studies of synthetic peptides derived from the third intracellular loop of the beta-adrenoceptor.
http://www.ncbi.nlm.nih.gov/corehtml/query/egifs/http:--linkinghub.elsevier.com-ihub-images-PubMedLink.gif Related Articles NMR and circular dichroism studies of synthetic peptides derived from the third intracellular loop of the beta-adrenoceptor.
FEBS Lett. 1995 Jan 23;358(2):133-6
Authors: Jung H, Windhaber R, Palm D, Schnackerz KD
The C-terminal part of the third intracellular loop of the beta-adrenoceptor is capable...
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[NMR paper] Synthesis and interaction studies of 13C labeled lactone derivatives with a model pro
Synthesis and interaction studies of 13C labeled lactone derivatives with a model protein using 13C NMR.
http://www.ncbi.nlm.nih.gov/corehtml/query/egifs/http:--linkinghub.elsevier.com-ihub-images-PubMedLink.gif Related Articles Synthesis and interaction studies of 13C labeled lactone derivatives with a model protein using 13C NMR.
Bioorg Med Chem. 1993 Nov;1(5):389-97
Authors: Franot C, Benezra C, Lepoittevin JP
Two molecules 9 and 14, representatives of two series of electrophilic lactone derivatives, have been synthesized, and labeled with...
A few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives.
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