Practical syntheses of pyridinolines, important amino acidic biomarkers of collagen health.
The paper reports some successful results on the first fully stereoselective total synthesis of the collagen cross-link pyridinolines. All stereogenic centers are stereoselectively introduced using Williams glycine template methodology, and oxazinones are used as a source of chirality and as easily removable protecting groups of the amino acidic functionalities during the assembly of the pyridinoline nucleus.
Allevi
Pietro
P
Dipartimento di Chimica, Biochimica e Biotecnologie per la Medicina, Università di Milano, via Saldini 50, I-20133 Milano, Italy.
Cribiù
Riccardo
R
Giannini
Elios
E
Anastasia
Mario
M
D000596:Amino Acids / Q000138:chemical synthesis* / Q000378:metabolism; D015415:Biomarkers / Q000737:chemistry* / Q000378:metabolism; D002625:Chemistry, Organic / Q000379:methods*; D003094:Collagen / Q000378:metabolism*; D006801:Humans; D006901:Hydroxylysine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D000596:Amino Acids; D015415:Biomarkers; D006901:Hydroxylysine; C015484:pyridinoline; C036020:deoxypyridinoline; D003094:Collagen