Journal
ACS CHEMICAL BIOLOGY
Volume 7, Issue 9, Pages 1482-1487Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cb300187t
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Funding
- National Science and Engineering Research Council of Canada (NSERC)
- Alberta Glycomics Centre
- SENTINEL Bioactive paper network
- Grand Challenges Canada (Rising Star in Global Health award)
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Phage display is a powerful technology that enables the discovery of peptide ligands for many targets. Chemical modification of phage libraries have allowed the identification of ligands with properties not encountered in natural polypeptides. In this report, we demonstrated the synthesis of 2 X 10(8) genetically encoded glycopeptides from a commercially available phage-displayed peptide library (Ph.D.-7) in a two-step, one-pot reaction in <1.5 h. Unlike previous reports, we bypassed genetic engineering of phage. The glycan moiety was introduced via an oxime ligation following oxidation of an N-terminal Ser/Thr; these residues are present in the peptide libraries at 20-30% abundance. The construction of libraries was facilitated by simple characterization, which directly assessed the yield and regioselectivity of chemical reactions performed on phage. This quantification method also allowed facile yield determination of reactions in 109 distinct molecules. We envision that the methodology described herein will find broad application in the synthesis of custom chemically modified phage libraries.
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