199116-19-3Relevant academic research and scientific papers
A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant
Wang, Zhi-Guang,Warren, J. David,Dudkin, Vadim Y.,Zhang, Xufang,Iserloh, Ulrich,Visser, Michael,Eckhardt, Matthias,Seeberger, Peter H.,Danishefsky, Samuel J.
, p. 4954 - 4978 (2007/10/03)
The total synthesis of an H-type blood group determinant in a model biological setting is described. The construct is comprised of a high mannose core structure with projecting lactose spacers, culminating in a two-copy presentation of the H-type blood group determinant itself. Key reactions that were used in this construction include sulfonamidohydroxylation (see 15→18) and benzoate-directed glycosylation via an activated thiophenyl donor (see 34→36). Another key strategic element involved the epimerization of an interior core glucoside to reach the β-mannoside (see 37→38) required in the ring C sugar of the high mannose core.
A highly convergent total synthetic route to glycopeptides carrying a high-mannose core pentasaccharide domain N-linked to a natural peptide motif
Danishefsky, Samuel J.,Hu, Shuanghua,Cirillo, Pier F.,Eckhardt, Matthias,Seeberger, Peter H.
, p. 1617 - 1628 (2007/10/03)
N-Linked glycopeptides were synthesized by condensation of a high-mannose anomeric amine bearing a pentasaccharide with aspartic-acid-containing tri- and pentapeptides through the agency of IIDQ. The pentasaccharide portion, corresponding to the 'core' re
