Solid-Phase Synthesis and Evaluation of Glycopeptide Fragments from Rat Epididymal Cysteine-Rich Secretory Protein-1 (Crisp-1) ？ 英文参考文献.docVIP

Molecules 2010, 15, 6399-6410; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Solid-Phase Synthesis and Evaluation of Glycopeptide Fragments from Rat Epididymal Cysteine-Rich Secretory Protein-1 (Crisp-1) ? Mian Liu 1,?, David W. Hamilton 2 and George Barany 1,* 1 Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA 2 Department of Genetics, Cell Biology and Development, University of Minnesota, Minneapolis, MN 55455, USA ? This work is dedicated to Professor Gary R. Gray on the occasion of his retirement after 38 years of teaching and research on carbohydrates as a member of the Chemistry faculty at the University of Minnesota ?Twin Cities campus. ? Current address: Complex Carbohydrate Research Center, University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA. * Author to whom correspondence should be addressed; E-Mail: barany@; Tel.: +1-612-625-1028; Fax: +1-612-626-7541. Received: 17 May 2010; in revised form: 24 August 2010 / Accepted: 6 September 2010 / Published: 14 September 2010 Abstract: Three 18-residue peptides with the sequence Glp-Asp-Thr-Thr-Asp-Glu-Trp- Asp-Arg-Asp-Leu-Glu-Asn-Leu-Ser-Thr-Thr-Lys, taken from the N-terminus of the rat epididymal cysteine-rich secretory protein (Crisp-1) that is important in the fertilization process, were prepared by Fmoc solid-phase synthesis using a convergent strategy. These peptides were the parent sequence, plus two possible α-O-linked TN antigen-containing glycopeptides with a Thr(α-D-GalNAc) residue in place of either Thr3 or Thr4. During chain assembly, two deletion peptides [des-Asp2 and des-Thr(Ac3-α-D-GalNAc)] and one terminated peptide [N-acetylated 14-mer] arose, as did several peptides in which aspartimide formation had occurred at each of the four possible positions in the sequence. These by-products totaled ~20% of the desired product; they were reco