ArticleThe Journal of biological chemistry2019
Analyses of lysine aldehyde cross-linking in collagen reveal that the mature cross-link histidinohydroxylysinonorleucine is an artifact.
Article in The Journal of biological chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed, 57 citations in OpenAlex.
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- The Versatility of Collagen in Pharmacology: Targeting Collagen, Targeting with Collagen.International journal of molecular sciences · 2024Review
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- Exploring the Interplay between Polyphenols and Lysyl Oxidase Enzymes for Maintaining Extracellular Matrix Homeostasis.International journal of molecular sciences · 2023Review
- Collagen Extraction from Animal Skin.Biology · 2022Review
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- Age-related type I collagen modifications reveal tissue-defining differences between ligament and tendon.Matrix biology plus · 2021Article
- Collagen Bioinks for Bioprinting: A Systematic Review of Hydrogel Properties, Bioprinting Parameters, Protocols, and Bioprinted Structure Characteristics.Biomedicines · 2021Review
- Abnormal Bone Collagen Cross-Linking in Osteogenesis Imperfecta/Bruck Syndrome Caused by Compound HeterozygousJBMR plus · 2021Article
- Cross your heart? Collagen cross-links in cardiac health and disease.Cellular signalling · 2021Review
- A tough act to follow: collagen hydrogel modifications to improve mechanical and growth factor loading capabilities.Materials today. Bio · 2021Review
- Increased Fibrosis in a Mouse Model of Anti-Laminin 332 Mucous Membrane Pemphigoid Remains Unaltered by Inhibition of Aldehyde Dehydrogenase.Frontiers in immunology · 2021Article
- Sea Cucumber Derived Type I Collagen: A Comprehensive Review.Marine drugs · 2020Review
- Does Subunit Composition Influence the Intermolecular Crosslinking of Fish Collagen? A Study with Hake and Blue Shark Skin Collagens.Polymers · 2020Article
- Mechanical stretching changes crosslinking and glycation levels in the collagen of mouse tail tendon.The Journal of biological chemistry · 2020Article
- Age-related changes in the physical properties, cross-linking, and glycation of collagen from mouse tail tendon.The Journal of biological chemistry · 2020Article
- Activin-mediated alterations of the fibroblast transcriptome and matrisome control the biomechanical properties of skin wounds.Nature communications · 2020Article
- ISSLS PRIZE IN BASIC SCIENCE 2020: Beyond microstructure-circumferential specialization within the lumbar intervertebral disc annulus extends to collagen nanostructure, with counterintuitive relationships to macroscale material properties.European spine journal : official publication of the European Spine Society, the European Spinal Deformity Society, and the European Section of the Cervical Spine Research Society · 2020Article
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Abstract
Lysyl oxidase-generated intermolecular cross-links are essential for the tensile strength of collagen fibrils. Two cross-linking pathways can be defined, one based on telopeptide lysine aldehydes and another on telopeptide hydroxylysine aldehydes. Since the 1970s it has been accepted that the mature cross-linking structures on the lysine aldehyde pathway, which dominates in skin and cornea, incorporate histidine residues. Here, using a range of MS-based methods, we re-examined this conclusion and found that telopeptide aldol dimerization is the primary mechanism for stable cross-link formation. The C-telopeptide aldol dimers formed labile addition products with glucosylgalactosyl hydroxylysine at α1(I)K87 in adjacent collagen molecules that resisted borohydride reduction and after acid hydrolysis produced histidinohydroxylysinonorleucine (HHL), but only from species with a histidine in their α1(I) C-telopeptide sequence. Peptide MS analyses and the lack of HHL formation in rat and mouse skin, species that lack an α1(I) C-telopeptide histidine, revealed that HHL is a laboratory artifact rather than a natural cross-linking structure. Our experimental results also establish that histidinohydroxymerodesmosine is produced by borohydride reduction of N-telopeptide allysine aldol dimers in aldimine intermolecular linkage to nonglycosylated α1(I) K930. Borohydride reduction of the aldimine promotes an accompanying base-catalyzed Michael addition of α1(I) H932 imidazole to the α,β-unsaturated aldol. These aldehydes are intramolecular at the N terminus but at the C terminus they can be both intramolecular and intermolecular according to present and earlier findings.
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