Postsynthetic modification of peptoids via the  S uzuki‐ M iyaura cross‐coupling reaction | Zendy

Nam Ho Yeon | Zendy; Seo Jiwon | Zendy

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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.

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