Matches in SemOpenAlex for { <https://semopenalex.org/work/W2055410421> ?p ?o ?g. }
Showing items 1 to 83 of
83
with 100 items per page.
- W2055410421 endingPage "686" @default.
- W2055410421 startingPage "682" @default.
- W2055410421 abstract "The chemical synthesis and use of O-sulfated hydroxy amino acids in solid-phase peptide synthesis has long been a difficult and delicate task for peptide chemists due to the intrinsic acid lability of the O-sulfate linkage. In this report, a significantly improved method for the introduction and acid-stabilization of sulfate groups onto serine, threonine, and hydroxyproline residues is described. In all three cases, the optimal sulfation conditions were found to be 5 equivalents of sulfur trioxide–N,N-dimethylformamide (SO3·DMF) complex in DMF under anhydrous conditions. The addition of tetrabutylammonium (TBA) counter-ions during work-up served as a powerful O-sulfate stabilization agent. The preparation of Fmoc-Ser(SO3−N+Bu4)-OH 3, Fmoc-Thr(SO3−N+Bu4)-OH 4 and Fmoc-Hyp(SO3−N+Bu4)-OH 6 building blocks gave stable pure products with good solubilities in organic solvents in reproducible, high yields. Importantly, the tetrabutylammonium salts of O-sulfated hydroxy amino acids minimized the desulfation during fluoren-9-ylmethoxycarbonyl (Fmoc)-based peptide synthesis, TFA cleavage, and reversed-phase HPLC purification. Stability experiments with 95% TFA at room temperature showed that for all three derivatives desulfation was less than 5% after standard times for peptide deprotection and resin-cleavage times. In contrast to previous approaches that usually involve the use of sodium and barium salts, the synthesis and mass spectrometric analysis of sulfated amino acids and sulfate peptides was much improved by the presence of tetrabutylammonium salts." @default.
- W2055410421 created "2016-06-24" @default.
- W2055410421 creator A5008925360 @default.
- W2055410421 creator A5030310636 @default.
- W2055410421 creator A5045104289 @default.
- W2055410421 date "2002-02-05" @default.
- W2055410421 modified "2023-09-26" @default.
- W2055410421 title "Preparation of novel O-sulfated amino acid building blocks with improved acid stability for Fmoc-based solid-phase peptide synthesis" @default.
- W2055410421 cites W1952295494 @default.
- W2055410421 cites W1970004497 @default.
- W2055410421 cites W1981665139 @default.
- W2055410421 cites W1985274757 @default.
- W2055410421 cites W1988184759 @default.
- W2055410421 cites W1990332976 @default.
- W2055410421 cites W1994470606 @default.
- W2055410421 cites W2007968374 @default.
- W2055410421 cites W2018408953 @default.
- W2055410421 cites W2037446939 @default.
- W2055410421 cites W2045992813 @default.
- W2055410421 cites W2052517893 @default.
- W2055410421 cites W2078420278 @default.
- W2055410421 cites W2087889708 @default.
- W2055410421 cites W2091780742 @default.
- W2055410421 cites W2313815794 @default.
- W2055410421 cites W2335117233 @default.
- W2055410421 cites W295484251 @default.
- W2055410421 doi "https://doi.org/10.1039/b107320f" @default.
- W2055410421 hasPublicationYear "2002" @default.
- W2055410421 type Work @default.
- W2055410421 sameAs 2055410421 @default.
- W2055410421 citedByCount "15" @default.
- W2055410421 countsByYear W20554104212012 @default.
- W2055410421 countsByYear W20554104212014 @default.
- W2055410421 countsByYear W20554104212015 @default.
- W2055410421 countsByYear W20554104212020 @default.
- W2055410421 countsByYear W20554104212021 @default.
- W2055410421 countsByYear W20554104212023 @default.
- W2055410421 crossrefType "journal-article" @default.
- W2055410421 hasAuthorship W2055410421A5008925360 @default.
- W2055410421 hasAuthorship W2055410421A5030310636 @default.
- W2055410421 hasAuthorship W2055410421A5045104289 @default.
- W2055410421 hasConcept C155138218 @default.
- W2055410421 hasConcept C178790620 @default.
- W2055410421 hasConcept C185592680 @default.
- W2055410421 hasConcept C2776469878 @default.
- W2055410421 hasConcept C2777712214 @default.
- W2055410421 hasConcept C2779281246 @default.
- W2055410421 hasConcept C2779809887 @default.
- W2055410421 hasConcept C2780471494 @default.
- W2055410421 hasConcept C515207424 @default.
- W2055410421 hasConcept C55493867 @default.
- W2055410421 hasConcept C60002323 @default.
- W2055410421 hasConceptScore W2055410421C155138218 @default.
- W2055410421 hasConceptScore W2055410421C178790620 @default.
- W2055410421 hasConceptScore W2055410421C185592680 @default.
- W2055410421 hasConceptScore W2055410421C2776469878 @default.
- W2055410421 hasConceptScore W2055410421C2777712214 @default.
- W2055410421 hasConceptScore W2055410421C2779281246 @default.
- W2055410421 hasConceptScore W2055410421C2779809887 @default.
- W2055410421 hasConceptScore W2055410421C2780471494 @default.
- W2055410421 hasConceptScore W2055410421C515207424 @default.
- W2055410421 hasConceptScore W2055410421C55493867 @default.
- W2055410421 hasConceptScore W2055410421C60002323 @default.
- W2055410421 hasIssue "5" @default.
- W2055410421 hasLocation W20554104211 @default.
- W2055410421 hasOpenAccess W2055410421 @default.
- W2055410421 hasPrimaryLocation W20554104211 @default.
- W2055410421 hasRelatedWork W1974040309 @default.
- W2055410421 hasRelatedWork W1985397541 @default.
- W2055410421 hasRelatedWork W2038603120 @default.
- W2055410421 hasRelatedWork W2055410421 @default.
- W2055410421 hasRelatedWork W2093864716 @default.
- W2055410421 hasRelatedWork W2408920609 @default.
- W2055410421 hasRelatedWork W2481268306 @default.
- W2055410421 hasRelatedWork W2952527835 @default.
- W2055410421 hasRelatedWork W2955591537 @default.
- W2055410421 hasRelatedWork W4239576100 @default.
- W2055410421 isParatext "false" @default.
- W2055410421 isRetracted "false" @default.
- W2055410421 magId "2055410421" @default.
- W2055410421 workType "article" @default.