- Comparison of various coupling reagents in solid-phase aza-peptide synthesis
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Aza-peptides are promising drug leads, however extensive study of their properties is hampered by low yielding aza-peptide bond formation during conventional Fmoc SPPS. The kinetics of aza-peptide bond formation in the model peptide H-Ala-AzAla-Phe-NHsub
- Aruj?e, Meeli,Ploom, Anu,Mastitski, Anton,J?rv, Jaak
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- Application of 2,2′-dipyridyl disulfide-mediated thiazolidine ring-opening reaction to glycoprotein synthesis: Total chemical synthesis of evasin-3
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Thiazolidine ring-opening reaction is one of the key steps in protein chemical synthesis via sequential native chemical ligation strategy. We recently developed a novel thiazolidine ring-opening reaction with 2,2′-dipyridyl disulfide (DPDS). In order to i
- Katayama, Hidekazu,Nagata, Koji
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- A novel family of onium salts based upon isonitroso meldrum's acid proves useful as peptide coupling reagents
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A new family of uronium salts (HTMU, HMMU, and HDmPyMU) based on isonitroso Meldrum's acid (HONM) are reported as stand-alone coupling reagents. Amide bond formation with the use of these reagents occurred more quickly than that with other uronium salts as a result of the presence of a neighboring group effect with a cyclic structure. Thus, these novel onium salts were often more effective in the acylation of poor nucleophiles and in the control of optical purity than related Oxyma- and benzotriazole-based reagents. Among the HONM derivatives, HMMU showed the best performance in reducing racemization and assembling demanding sequences such as the Aib-ACP decapeptide or analogues of Leu-enkephalin pentapeptide, Furthermore, the scope and limitations of the use of HONM as an additive in combination with carbodiimides is discussed.
- El-Faham, Ayman,Subiros-Funosas, Ramon,Albericio, Fernando
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experimental part
p. 3641 - 3649
(2010/09/03)
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- Cinnamic aldehyde derived probes for the active site labelling of pathogenesis associated enzymes
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Michael acceptor based natural product derived probes are selective and sensitive chemical tools for the identification and characterization of pathologically relevant enzymes in MRSA.
- Pitscheider, Maximilian,Sieber, Stephan A.
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supporting information; experimental part
p. 3741 - 3743
(2009/12/01)
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- Synthesis and properties of a new conformational antigen which models an extracellular region of β1-adrenoreceptor
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Two fragments corresponding to the 125-133 and 206-218 sequences of a molecule of the β1-adrenoreceptor (autoantibodies to this protein are often found in patients with dilated cardiomyopathy) were synthesized by the solid phase method with the use of Fmoc technology. Two new conformational antigens were prepared by directed (regioselective) and undirected (spontaneous) formation of intramolecular and intermolecular disulfide bridges between the corresponding cysteine residues of the synthesized peptides. One of these antigens consisted of a mixture of disulfide isomers, and another antigen was an isomer with a natural arrangement of S-S bridges. Immunosorbents were obtained by immobilization of the synthesizes antigens on the bromocyanogen-activated sepharose and applied to the removal of autoantibodies in a β1- adrenoreceptor from the blood plasma of patients. We demonstrated that the sorbents on the basis of the conformational antigens were more effective in comparison with those containing linear peptide precursors.
- Sidorova,Pal'Keeva,Molokoedov,Az'Muko,Sekridova,Ovchinnikov,Levashov,Afanasieva,Berestetskaya,Afanasieva,Razova,Bespalova,Pokrovskii
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experimental part
p. 285 - 295
(2010/06/16)
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- Fluorine and rhenium substituted ghrelin analogues as potential imaging probes for the growth hormone secretagogue receptor
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In our effort to create imaging probes targeting the growth hormone secretagogue receptor (GHSR), we now report on the design and synthesis of fluorine and rhenium containing ghrelin analogues through modification of the n-octanoyl Ser-3 side chain. Fluor
- Rosita, Dina,Dewit, Matthew A.,Luyt, Leonard G.
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experimental part
p. 2196 - 2203
(2010/03/26)
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- Peptides for inhibition of apoptosis and pharmaceutical compositions containing them
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The present invention relates to an isolated and purified peptide of the RY domain having an amino acid sequence of general formula (I) comprising a sequence of the following amino acids: X1—X2—X3—X4—X1/su
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Page/Page column 8-9
(2008/06/13)
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- A liquid-phase peptide synthesis in cyclohexane-based biphasic thermomorphic systems
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Combinations of typical organic solvents composed of cyclohexane and qualified aprotic polar organic solvents were found to realize an effecitive, biphasic thermomorphic system in arbitrary ratios of upper and lower phases that enable a practical applicat
- Chiba, Kazuhiro,Kono, Yusuke,Kim, Shokaku,Nishimoto, Kohsuke,Kitano, Yoshikazu,Tada, Masahiro
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p. 1766 - 1767
(2007/10/03)
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- Chemo-enzymatic synthesis of Fmoc-peptide fragments
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Optically pure Fmoc-peptide fragments have been prepared via dicyclohexylcarbodiimide coupling of N-protected amino acids with amino cid esters, followed by enzyme-catalyzed ester hydrolysis by alcalase with a high concentration of organic solvent in a hi
- Chen,Hsiao,Chang,Wang
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p. 391 - 398
(2007/10/02)
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- Studies on Conformationally Restricted, Disiloxane Bridged Analogues of the Enkephalins
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Solution-phase synthesis of protected 2, Ser5>- and 2, Ser5>-enkephalins, followed by treatment with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane i2Si(Cl)-O-Si(Cl)Pri2> in base have yielded cyclic bridged disiloxane analogues showing biological activity in an in vitro assay.Highfield (1)H n.m.r. studies augmented by n.O.e. difference spectroscopy, temperature dependence studies of the amide protons, and the use of computer graphics support the presence of a 2-->5 H-bonded β-bend conformation for the most biologically potent of the cyclic analogues.
- Davies, John S.,Tremeer, E. John,Treadgold, Richard C.
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p. 1107 - 1116
(2007/10/02)
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