- Efficient synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate as a precursor of PET radiotracer [18F]FPGLN
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This study describes a convenient protocol for the synthesis of (2S)-tert-butyl 2-(2-bromopropanamido)-5-oxo-5-(tritylamino)pentanoate, which can serve as an appropriate precursor of (2S)-5-amino-2-(2-[18F]fluoropropanamido)-5-oxopentanoic acid
- Liu, Shaoyu,Tang, Xiaolan,Nie, Dahong,Jiang, Shende,Tang, Ganghua
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supporting information
p. 1136 - 1141
(2017/06/09)
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- Probing the role of backbone hydrogen bonds in protein-peptide interactions by amide-to-ester mutations
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One of the most frequent protein-protein interaction modules in mammalian cells is the postsynaptic density 95/discs large/zonula occludens 1 (PDZ) domain, involved in scaffolding and signaling and emerging as an important drug target for several diseases
- Eildal, Jonas N. N.,Hultqvist, Greta,Balle, Thomas,Stuhr-Hansen, Nicolai,Padrah, Shahrokh,Gianni, Stefano,Stromgaard, Kristian,Jemth, Per
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supporting information
p. 12998 - 13007
(2013/09/24)
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- Total synthesis and stereochemical reassignment of tasiamide B
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The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of Nα-Me-Gln and led to a reassignment of the Nα-Me-L-Phe of tasiamide B to be N α-Me-D-Phe, which was also supported by 1D and 2D NMR. Copyright
- Sun, Tiantian,Zhang, Wei,Zong, Chengli,Wang, Peng,Li, Yingxi
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experimental part
p. 364 - 374
(2011/03/22)
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- Tuning glutamine binding modes in Gd-DOTA-based probes for an improved MRI visualization of tumor cells
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Three new magnetic resonance imaging probes that target glutamine transporters have been synthesized. They consist of a Gd-DOTA-monoamide moiety (DOTA = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) linked through a six carbon atom chain to a
- Stefania, Rachele,Tei, Lorenzo,Barge, Alessandro,Crich, Simonetta Geninatti,Szabo, Ibolya,Cabella, Claudia,Cravotto, Giancarlo,Aime, Silvio
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experimental part
p. 76 - 85
(2009/07/17)
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- Tripeptide aldehyde inhibitors of human rhinovirus 3C protease: Design, synthesis, biological evaluation, and cocrystal structure solution of P1 glutamine isosteric replacements
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The investigation of tripeptide aldehydes as reversible covalent inhibitors of human rhinovirus (HRV) 3C protease (3CP) is reported. Molecular models based on the apo crystal structure of HRV-14 3CP and other trypsin- like serine proteases were constructe
- Webber, Stephen E.,Okano, Koji,Little, Thomas L.,Reich, Siegfried H.,Xin, Yue,Fuhrman, Sheila A.,Matthews, David A.,Love, Robert A.,Hendrickson, Thomas F.,Patick, Amy K.,Meador III, James W.,Ferre, Rose Ann,Brown, Edward L.,Ford, Clifford E.,Binford, Susan L.,Worland, Stephen T.
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p. 2786 - 2805
(2007/10/03)
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- Partially modified and retro-inverted tetrapeptides analogues of C-reactive protein fragments
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Retro-inverted tetrapeptides of formula I STR1 wherein R is a hydrogen atom or the side-chain of threonine; R1 is the side-chain of arginine, leucine or glutamine; and R2 is a hydrogen atom or a metabolically perishable acyl group; with the proviso that when R1 is the side-chain of arginine, R cannot be the side-chain of threonine; diastereo-isomeric forms and pharmacologically acceptable salts, esters and amides thereof. These compounds are useful as immuno-stimulating agents.
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- Protected amino acids and process for the preparation thereof
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Compounds of the formula I, STR1 in which 'R1 is an amino protective group, and n stands for 1 or 2, R1 denotes hydrogen or an amino protective group, R2 denotes hydrogen or a carboxyl protective group and R3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R2 stands for hydrogen, are described. These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.
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- Protection of carboxamide functions by the trityl residue. Application to peptide synthesis
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Carboxamide functions may be tritylated by an acid-catalyzed reaction with triphenylmethanol and acetic anhydride in glacial acetic acid. The ω-trityl group of asparagine and glutamine is cleavable by TFA, but stable to strong mineral acids in aqueous solution, as well as to nucleophiles and bases. In peptide syntheses, it is ideally suited for combination with side-chain protections of the t.butyl-type.
- Sieber,Riniker
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p. 739 - 742
(2007/10/02)
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