Abstract
The Asn glycopeptide 1, when compared to analogs Gln 2 and (D)Thr 3, displays intramolecular sugar‐peptide interactions in a DMSO‐d6/CD2Cl2 organic solvent mixture. A comparative 1H NMR study between Asn 1 and Gln 2 shows sequence‐specific changes in the sugar's C5–C6 rotamer population. The diastereomeric glycopeptide 3 containing a (D)‐Thr3 residue also shows some significantly different sugar 1H and 13C NMR chemical shifts compared to the parent glycopeptide 1. The GlcNAc sugar attached to the Asn1 sidechain is able to sense the stereochemistry at the remote Thr3 residue.
Acknowledgment
We thank the NIH (R29 CA16644) for funding this work. JD also thanks the Dreyfus Foundation for a Teacher‐Scholar Award.