A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant Journal Article
| Authors: | Wang, Z. G.; Warren, J. D.; Dudkin, V. Y.; Zhang, X.; Iserloh, U.; Visser, M.; Eckhardt, M.; Seeberger, P. H.; Danishefsky, S. J. |
| Article Title: | A highly convergent synthesis of an N-linked glycopeptide presenting the H-type 2 human blood group determinant |
| Abstract: | 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. © 2006 Elsevier Ltd. All rights reserved. |
| Keywords: | enzyme linked immunosorbent assay; alcohol; structure analysis; reaction analysis; glycopeptide; peptide synthesis; stereochemistry; sugar; pentasaccharide; hydroxylation; blood group; benzoic acid; lactose; mannose; mannoside; thioglycoside; trisaccharide |
| Journal Title: | Tetrahedron |
| Volume: | 62 |
| Issue: | 20 |
| ISSN: | 0040-4020 |
| Publisher: | Elsevier Inc. |
| Date Published: | 2006-05-15 |
| Start Page: | 4954 |
| End Page: | 4978 |
| Language: | English |
| DOI: | 10.1016/j.tet.2006.02.080 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 23" - "Export Date: 4 June 2012" - "CODEN: TETRA" - "Source: Scopus" |
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