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A fluorescent peptoid pH‐sensor
Author(s) -
Fuller Amelia A.,
Holmes Courtney A.,
Seidl Frederick J.
Publication year - 2013
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.22242
Subject(s) - peptoid , chemistry , fluorophore , fluorescence , side chain , combinatorial chemistry , peptide , biophysics , organic chemistry , polymer , biochemistry , physics , quantum mechanics , biology
Peptoids, N ‐substituted glycine oligomers, can adopt stable three‐dimensional structures and have found diverse application as peptide surrogates and as nanomaterials. In this report, we have expanded peptoid function to include pH sensing by coupling pH‐induced peptoid conformational changes with fluorescence intensity changes. We report two new peptoids ( 2 and 3 ) that comprise carboxylic‐acid functionalized side chains and undergo conformational rearrangement in response to pH. Peptoids 2 and 3 are also labeled at one side‐chain with an environmentally sensitive fluorophore, 4‐ N , N‐ dimethylamino‐1,8‐naphthalimide (4DMN). The fluorescence intensity of 2 varies 24‐fold over the pH range studied. These spectroscopic properties make 2 a sensitive, biocompatible pH sensor. © 2013 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 100: 380–386, 2013.