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DOI: 10.1055/s-0043-1775486
Total Synthesis of Deoxypyridinoline and Deoxypyridinoline-13C2,15N1
This work was supported by the KOSÉ Cosmetology Research Foundation.

Abstract
Collagen fibers, which make up 30% of all proteins in vertebrates, are extracellular matrix proteins that provide mechanical strength to connective tissues such as skin and bone, forming the structural foundation of the body. Deoxypyridinoline, a collagen cross-linking amino acid first isolated from bovine bone in 1982, is released into the bloodstream during bone metabolism alongside degraded bone tissue. This makes it a promising biomarker for quantitatively assessing diseases associated with abnormal bone resorption. In this study, we achieved the total synthesis of deoxypyridinoline from commercially available amino acids in five steps with an overall yield of 20%. This synthetic method provides a scalable alternative to isolating the compound from natural sources. As part of ongoing research into its use as a biomarker, we also synthesized isotopically labeled deoxypyridinoline-13C2,15N1, which can be used as an internal standard for quantitative analysis.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775486.
Copies of 1H and 13C NMR spectra for new compounds are provided.
- Supporting Information
Publikationsverlauf
Eingereicht: 07. April 2025
Angenommen nach Revision: 22. April 2025
Artikel online veröffentlicht:
03. Juni 2025
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References
- 1 Current address: Department of Applied Chemistry, Chuo University, Tokyo, Japan.
- 2 Gaar J, Naffa R, Brimble M. Org. Chem. Front. 2020; 7: 2789
- 3a Gross J, Schmitt FO. J. Exp. Med. 1948; 88: 555
- 3b Campos LD, Santos Junior VA, Pimentel JD, Carregã GL. F, Cazarin CB. B. Heliyon 2023; 9: e14961
- 4 Ogawa T, Ono T, Tsuda M, Kawanishi Y. Biochem. Biophys. Res. Commun. 1982; 107: 1252
- 5 Adamczyk M, Johnson DD, Reddy RE. Tetrahedron 1999; 55: 63
- 6 Tang JC. Y, Dutton JJ, Piec I, Green D, Fisher E, Washbourne CJ, Fraser WD. Clin. Mass Spectrom. 2016; 1: 11
- 7 Adamczyk M, Johnson DD, Reddy RE. Tetrahedron: Asymmetry 2000; 11: 2289
- 8 Adamczyk M, Johnson DD, Reddy RE. Tetrahedron Lett. 1999; 40: 8993
- 9 Allevi P, Longo A, Anastasia M. Chem. Commun. 1999; 559
- 10 Allevi P, Femia EA, Rota P, Costa ML, Anastasia M. Tetrahedron: Asymmetry 2008; 19: 2470
- 11 Allevi P, Galligani M, Anastasia M. Tetrahedron: Asymmetry 2002; 13: 1901
- 12 Ishii H, Shigeta R, Oishi K, Usuki T. Tetrahedron Lett. 2025; 158: 155508
- 13 Tanigawa T, Komatsu A, Usuki T. Bioorg. Med. Chem. Lett. 2015; 25: 2046
- 14 Hirose M, Kobayashi T, Tanaka N, Mikagi A, Wachi H, Mizutani Y, Usuki T. Bioorg. Med. Chem. 2021; 52: 116519
- 15 Mikagi A, Tashiro R, Inoue T, Anzawa R, Imura A, Tanigawa T, Ishida T, Inoue T, Niizuma K, Tominaga T, Usuki T. RSC Adv. 2022; 12: 31679
- 16 Sugimura T, Komatsu A, Koseki Y, Usuki T. Tetrahedron Lett. 2014; 55: 6343
- 17 Prileschajew N. Ber. Dtsch. Chem. Ges. 1909; 42: 4811
- 18 Appel R. Angew. Chem., Int. Ed. Engl. 1975; 14: 801