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Postsynthetic modification of peptoids via the S uzuki‐ M iyaura cross‐coupling reaction
Author(s) -
Nam Ho Yeon,
Seo Jiwon
Publication year - 2016
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.22747
Subject(s) - chemistry , peptoid , palladium , coupling reaction , combinatorial chemistry , conjugated system , pyrene , ligand (biochemistry) , side chain , solid phase synthesis , catalysis , polymer chemistry , organic chemistry , peptide , polymer , biochemistry , receptor
We developed a new method for modifying the side chains of peptoids on a solid phase resin, employing the palladium‐catalyzed Suzuki‐Miyaura cross‐coupling reaction. Optimized conditions using Pd(PPh 3 ) 4 and K 2 CO 3 in the presence of Buchwald's SPhos ligand provided a high conversion in the coupling reaction. The usefulness of this method was demonstrated by synthesis of a two pyrene‐conjugated peptoid helix, which exhibited an interesting excimer formation. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 82–88, 2016.