186020-93-9Relevant academic research and scientific papers
Heating and microwave assisted SPPS of C-terminal acid peptides on trityl resin: The truth behind the yield
Echalier, Cecile,Al-Halifa, Soultan,Kreiter, Aude,Enjalbal, Christine,Sanchez, Pierre,Ronga, Luisa,Puget, Karine,Verdie, Pascal,Amblard, Muriel,Martinez, Jean,Subra, Gilles
, p. 1395 - 1403 (2014/01/06)
Despite correct purity of crude peptides prepared on trityl resin by Fmoc/tBu microwave assisted solid phase peptide synthesis, surprisingly, lower yields than those expected were obtained while preparing C-terminal acid peptides. This could be explained
A novel protecting group for constructing combinatorial peptide libraries
Tamiaki, Hitoshi,Obata, Tomoyuki,Azefu, Yasuo,Toma, Kazunori
, p. 733 - 738 (2007/10/03)
3,4,5-Tris(octadecyloxy)benzyl alcohol, HO-Bzl(OC18)3, was prepared from gallic acid and stearyl bromide. Using conventional step-wise elongation, N,C-protected peptides, Fmoc - AAn - ... - AA1 - OBzl(OC18)3, were synthesized. The substituted benzyl esters were selectively cleaved by a treatment with 4 M hydrogen chloride in ethyl acetate to give Fmoc - AAn - ... - AA1 - OH and HO - Bzl(OC18)3. Thus, the substituted benzyl group is effective for the protection of C-terminal carboxyl groups in liquid-phase peptide synthesis. Because the substituted benzyl group has a moderately high molecular weight, Fmoc - AAn - ... - AA1 - OBzl(OC18)3 can be easily purified by size-exclusion chromatography; all protected peptides are eluted in the void fraction of a Sephadex LH-20 gel-filtration column. The combination of the carboxyl-protecting group Bzl(OC18)3 with simple purification by the gel-filtration gives a novel route for constructing combinatorial peptide libraries in the solution phase.
HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides
Seitz, Oliver,Kunz, Horst
, p. 813 - 826 (2007/10/03)
The recently developed allylic HYCRON anchor1 exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(0)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-αGalNAc-(TN)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.
