Peptide bond isosteres: ester or (E)-alkene in the backbone of the collagen triple helix.
[structure: see text] Collagen is the most abundant protein in animals. Interstrand N-H...O=C hydrogen bonds between backbone amide groups form a ladder in the middle of the collagen triple helix. Isosteric replacement of the hydrogen-bond-donating amide with an ester or (E)-alkene markedly decreases the conformational stability of the triple helix. Thus, this recurring hydrogen bond is critical to the structural integrity of collagen. In this context, an ester isostere confers more stability than does an (E)-alkene.
Jenkins
Cara L
CL
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, USA.
Vasbinder
Melissa M
MM
Miller
Scott J
SJ
Raines
Ronald T
RT
D000475:Alkenes / Q000737:chemistry*; D000595:Amino Acid Sequence; D003094:Collagen / Q000737:chemistry*; D004952:Esters; D006860:Hydrogen Bonding; D008958:Models, Molecular; D015394:Molecular Structure; D011487:Protein Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
D000475:Alkenes; D004952:Esters; D003094:Collagen