Rapid, continuous solution-phase peptide synthesis: Application to peptides of pharmaceutical interest
The Fmoc/TAEA and Bsmoc/TAEA methods for the rapid, continuous solution synthesis of peptide segments are shown to be applicable to the gram-scale synthesis of short peptides as well as, for the first time, to the synthesis of a relatively long (22-mer) segment, (hPTH 13-34). In the latter case the crude product was of significantly greater purity than a sample obtained via a solid-phase protocol. The Bsmoc methodology was optimized by a new technique involving filtration of the growing partially deprotected peptide at each coupling-deprotection cycle through a short column of silica gel.
Carpino, Louis A.,Ghassemi, Shahnaz,Ionescu, Dumitru,Ismail, Mohamed,Sadat-Aalaee, Dean,Truran, George A.,Mansour,Siwruk, Gary A.,Eynon, John S.,Morgan, Barry
Synthesis and Two-Dimensional (1)H and (13)C NMR Investigations of an Inhibitor of Hematopoietic Stem Cell Proliferation Ac--Ser-Asp-Lys-Pro-OH
The solid phase synthesis of the inhibitor of hematopoietic stem cell proliferation, Ac-Ser-Asp-Lys-Pro-OH, and its derivative Ac-Ala-Asp-Lys-Pro-OH is described. (1)H and (13)C NMR investigations demonstrate that both peptides show no prefered conformation in water solution.Both peptides exist in a Pro-cis-trans equilibrium ratio of 9 (trans) : 1 (cis).Thymosin β4 is believed to be the precursor molecule of the tetrapeptide Ac-SDKP.The attachment of the random coil tetrapeptide to a rigid helical fragment could facilitate its in vivo enzymatic cleavage. Key words: (13)C NMR; (1)H NMR; solid phase peptide synthesis; inhibitor stem cell proliferation.
Freund, Jens,Kapurniotu, Aroditi,Holak, Tadeusz A.,Lenfant, Maryse,Voelter, Wolfgang
p. 1324 - 1332
(2007/10/02)
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