2001
DOI: 10.1074/jbc.m009506200
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Structural Characterization of Pyrrolic Cross-links in Collagen Using a Biotinylated Ehrlich's Reagent

Abstract: The structures of pyrrolic forms of cross-links in collagen have been confirmed by reacting collagen peptides with a biotinylated Ehrlich's reagent. This reagent was synthesized by converting the cyano group of N-methyl-N-cyanoethyl-4-aminobenzaldehyde to a carboxylic acid, followed by conjugation with biotin pentylamine. Derivatization of peptides from bone collagen both stabilized the pyrroles and facilitated selective isolation of the pyrrole-containing peptides using a monomeric avidin column. Reactivity o… Show more

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Cited by 38 publications
(21 citation statements)
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“…Therefore, we cannot definitively state whether the observed changes in bone quality are applicable to other clinically relevant bone sites such as vertebra. Second, enzymatic mature pyrrole cross-links may be equally important as pyridinium cross-links [8,60]. Pyrrole crosslinks are unstable during acid hydrolysis and, therefore, we cannot measure them using our HPLC method.…”
Section: Raloxifene and Cross-linksmentioning
confidence: 99%
“…Therefore, we cannot definitively state whether the observed changes in bone quality are applicable to other clinically relevant bone sites such as vertebra. Second, enzymatic mature pyrrole cross-links may be equally important as pyridinium cross-links [8,60]. Pyrrole crosslinks are unstable during acid hydrolysis and, therefore, we cannot measure them using our HPLC method.…”
Section: Raloxifene and Cross-linksmentioning
confidence: 99%
“…The pyridinolines are spread equally between the N and C termini while the pyrroles appear to be concentrated at the N-terminal of the molecule (Knott et al 1995;Hanson and Eyre 1996;Brady and Robins 2001). This suggests a different function for the pyrrole and the pyridinoline cross-links.…”
Section: Bonementioning
confidence: 90%
“…4.2). The structure of the pyrroles have been confirmed as the biotinylated derivative employing mass spectrometry and, as in the case of the pyridinolines, there are both hydroxylysyl-pyrrole and lysyl-pyrrole present in some tissues, but they have not yet been isolated (Brady and Robins 2001).…”
Section: Pyrrolesmentioning
confidence: 91%
“…Recently, trivalent Prl cross-links having an identical chain topology with Pyr were identified (30,50,51). These were predominantly observed at the N-telo-to-helix site (30,50,51), concentrated at the loci ␣1-9 N ϫ ␣2-5 N ϫ ␣2-933 (30, 50) and ␣1-9 N ϫ ␣1-9 N ϫ ␣1-930/␣2-933 (51).…”
Section: Discussionmentioning
confidence: 99%
“…These were predominantly observed at the N-telo-to-helix site (30,50,51), concentrated at the loci ␣1-9 N ϫ ␣2-5 N ϫ ␣2-933 (30, 50) and ␣1-9 N ϫ ␣1-9 N ϫ ␣1-930/␣2-933 (51). Here, we characterized the Prl species ␣1-16 C ϫ ␣1-16 C ϫ ␣1-87/␣2-87 and ␣1-9 N ϫ ␣2-5 N ϫ ␣1-930/␣2-933.…”
Section: Discussionmentioning
confidence: 99%