Collagen is the most abundant protein in animals. The protein consists of a helix of three strands, each with sequence XY-Gly. Natural collagen is most stable when X is (2 S)-proline (Pro) and Y is (2 S, 4 R)-4-hydroxyproline (4 R-Hyp). We had shown previously that triple helices in which X is (2 S, 4 S)-4-fluoroproline (4 S-Flp) or Y is (2 S, 4 R)-4-fluoroproline (4 R- Flp) display hyperstability. This hyperstability arises from stereoelectronic effects that ...