Abstract
The Ala 1-Gly 28 glycopeptide fragment (28) of EPO was prepared by chemical synthesis as a single glycoform. Key steps in the synthesis include attachment of a complex dodecasaccharide (7) to a seven amino acid peptide via Lansbury aspartylation, native chemical ligation to join peptide 19 with the glycopeptide domain 18, and a selective desulfurization at the ligation site to reveal the natural Ala 19. This glycopeptide fragment (28) contains both the requisite N-linked dodecasaccharide and a C-terminal αthioester handle, the latter feature permitting direct coupling with a glycopeptide fragment bearing N-terminal Cys 29 without further functionalization.
Original language | English (US) |
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Pages (from-to) | 5438-5443 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 131 |
Issue number | 15 |
DOIs | |
State | Published - Apr 22 2009 |
All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry