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Biopolymers. 2015 Mar;104(2):110-5. doi: 10.1002/bip.22620.

4-ketoproline: An electrophilic proline analog for bioconjugation.

Author information

1
Graduate Program in Biophysics, University of Wisconsin-Madison, Madison, WI.

Abstract

Installing an electrophilic amino-acid residue can engender a peptide or protein with chemoselective reactivity. Such a modification to collagen, which is the most abundant protein in animals, could facilitate the development of new biomaterials. Collagen has an abundance of proline-like residues. Here, we report on the incorporation of an electrophilic proline congener, (2S)-4-ketoproline (Kep), into a collagen-mimetic peptide (CMP). An ab initio conformational analysis of Kep revealed its potential to be accommodated within a collagen triple helix. A synthetic CMP containing a Kep residue was indeed able to form a stable triple helix. Moreover, the condensation of its carbonyl group with aminooxy-biotin did not compromise the conformational stability of the triple helix. These data encourage the use of 4-ketoproline as an electrophilic congener of proline.

KEYWORDS:

4-ketoproline; 4-oxoproline; collagen; host-guest; oxime

PMID:
25656588
PMCID:
PMC4376587
DOI:
10.1002/bip.22620
[Indexed for MEDLINE]
Free PMC Article

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