Synthesis of reduced collagen crosslinks

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 12, 1999, Pages 1673-1676

  Van den Nieuwendijk, Adrianus M C H ^a   Benningshof, Jorg C J ^a   Wegmann, Volker ^a   Bank, Ruud A ^b   Te Koppele, Johan M ^b   Brussee, Johannes ^a   Van der Gen, Arne ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b TNO   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

COLLAGEN;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS LINKING; DIASTEREOISOMER; HYDROGENATION; PROTEIN SYNTHESIS; REACTION ANALYSIS;

ALKYLATION; COLLAGEN; CROSS-LINKING REAGENTS; DIPEPTIDES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0033591708     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00252-8     Document Type: Article

References (18)

1. a) Eyre, D.R.; Paz, A.; Gallop, P.M. Ann. Rev. Biochem. 1984, 53, 717-748.
2. b) Reiser, K.; McCormick, R.J.; Rucker, R.B. FASEB J. 1992, 6, 2439-2449.
3. c) Robins, S.P. Meth. Biochem. Anal. 1982, 28, 330-379.
4. d) Yamauchi M. Mechanic GL. Cross-linking of Collagen. In: Nimni ME (ed.), Collagen. Volume 1: Biochemistry. CRC Press, Boca Raton, 157-172 (1988).
5. Davis, N.R.; Bailey A.J. Biochem. J. 1972, 129, 91-96, and references cited.
6. Williams, R.M.; Sinclair P.J.; Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547-1557.
7. Aldrich Catalog Handbook of Fine Chemicals, p. 161 (1996-1997).
8. Van den Nieuwendijk, A.M.C.H.; Warmerdam, E.G.J.C.; Brussee, J.; Van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 801-806.
9. Aldehyde 5 was prepared in 70% yield from 1,4-butanediol via protection as the mono-THP ether and subsequent PCC oxidation to the aldehyde.
10. Cyanohydrin 6 was prepared from 1,3-propanediol via protection as the mono-benzyl ether, PCC oxidation to the aldehyde followed by HCN addition and protection of the cyanohydrin with TBS-Cl. (54% overall yield).
11. Zandbergen, P.; Van den Nieuwendijk, A.M.C.H.; Brussee, J.; Van der Gen, A.; Kruse, C.G. Tetrahedron 1992, 48, 3977-3982.
12. Zandbergen, P.; Brussee, J.; Van der Gen, A.; Kruse, C.G. Tetrahedron: Asymmetry 1992, 3, 769-774.
13. Baldwin, J.E.; Lee, V.; Schofield, C.J. Synlett 1992, 249-251.
14. 13C NMR; 22.6, 26.1, 30.6, 48.2, 55.8, 173.2.
15. Exact Mass experiments(ESI): a) LNL: M+H 276.18773; theoretical 276.18873, b) HLNL: M+H 292.17875; theoretical 292.17941, c) LNL diethyl ester: 332.25344; theoretical 332.25493.
16. Franzblau, C.; Faris, B.; Papaioannou, R. Biochemistry 1969, 8, 2833-2836.
17. Bank, R.A.; Jansen, E.J.; Beekman, B.; Te Koppele, J.M.; Anal. Biochem. 1996, 240, 167-176.
18. 13C NMR; 22.1, 25.5, 26.7, 30.0, 30.1, 30.2, 47.8, 52.7, 53.8, 66.8, 173.2, 173.3.