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Chemical Compound Review

SureCN8088     (2S)-3-hydroxypyrrolidine-2- carboxylic acid

Synonyms: AG-F-99586, CHEBI:20056, CTK0B1882, AC1L44ZU, 14916-76-8, ...
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Disease relevance of 3-Hydroxyproline


High impact information on 3-Hydroxyproline

  • Identification of collagen types was made by: reaction with specific antibodies to type I and IV collagens; electrophoretic mobility; sensitivity to reduction and to collagenase; analysis of the proportions of 3-hydroxyproline, 4-hydroxyproline and hydroxylysine; and CNBr peptides [4].
  • Possible explanations are: a more rapid turnover of basement membrane collagen than interstitial collagen or, alternatively, relatively greater resistance to the proteolytic cleavage of peptides containing 3-hydroxyproline [5].
  • The position of 3-hydroxyproline was investigated in the triplet sequences of peptides released by collagenase digestion of a collagen preparation from kidney cortex [6].
  • The secreted cathepsin L-like proteinases of the trematode, Fasciola hepatica, contain 3-hydroxyproline residues [7].
  • Heterogeneity with respect to 3-hydroxyproline and 4-hydroxyproline at a certain position in these peptides was assessed by tandem mass spectrometry based on the wn ion series in the CID spectra of these Lys-C peptides [8].

Biological context of 3-Hydroxyproline

  • Two further interruptions of the triple helix were indicated by single deletions of GLy or Yaa positions in the triplet structure (Gly-Xaa-Yaa)n. The two 3-hydroxyproline residues were found in position Xaa and are surrounded by homologous sequences [9].
  • After hydrolysis of the urine by 6 M HCl, 3-hydroxyproline is purified from many interfering substances by 2 steps of chromatography on Dowex 1 X8 resin equilibrated first in the acetate form and secondly in the OH- form [10].

Anatomical context of 3-Hydroxyproline


Associations of 3-Hydroxyproline with other chemical compounds


Gene context of 3-Hydroxyproline

  • The results suggest a decrease in the relative amount of the collagen component in the GBM of CNF patients, but a decrease in the relative amount of 3-hydroxyproline indicates that other changes also exist [15].
  • The renal excretion of 3 hydroxyproline (3 HYP) and 4 hydroxyproline (4 HYP) was investigated in control subjects and in patients with various renal diseases [2].
  • Comparison of GBM and TBM from the same kidneys showed at all ages that GBM contains more 3-hydroxyproline, neuraminic acids and mannose [16].


  1. Renal and microvascular effects of an aldose reductase inhibitor in experimental diabetes. Biochemical, functional and ultrastructural studies. Kassab, J.P., Guillot, R., Andre, J., Claperon, N., Bellon, G., Feldmann, G., Peyroux, J., Sternberg, M. Biochem. Pharmacol. (1994) [Pubmed]
  2. Increased renal excretion of 3 hydroxyproline in patients with active glomerular nephropathies and with polycystic renal disease. Chanard, J., Szymanowicz, A., Brunois, J.P., Toupance, O., Melin, J.P., Birembaut, P., Randoux, A., Borel, P.J. Clin. Nephrol. (1982) [Pubmed]
  3. Urinary 3-hydroxyproline excretion in Alport's syndrome: a non-invasive screening test? Bartosch, B., Vycudilik, W., Popow, C., Lubec, G. Arch. Dis. Child. (1991) [Pubmed]
  4. The localization and synthesis of some collagen types in developing mouse embryos. Adamson, E.D., Ayers, S.E. Cell (1979) [Pubmed]
  5. 3-Hydroxyproline content of normal urine. Adams, E., Ramaswamy, S., Lamon, M. J. Clin. Invest. (1978) [Pubmed]
  6. Sequence position of 3-hydroxyproline in basement membrane collagen. Isolation of glycyl-3-hydroxyprolyl-4-hydroxyproline from swine kidney. Gryder, R.M., Lamon, M., Adams, E. J. Biol. Chem. (1975) [Pubmed]
  7. The secreted cathepsin L-like proteinases of the trematode, Fasciola hepatica, contain 3-hydroxyproline residues. Wijffels, G.L., Panaccio, M., Salvatore, L., Wilson, L., Walker, I.D., Spithill, T.W. Biochem. J. (1994) [Pubmed]
  8. Differentiation of hydroxyproline isomers and isobars in peptides by tandem mass spectrometry. Kassel, D.B., Biemann, K. Anal. Chem. (1990) [Pubmed]
  9. Covalent structure of mouse type-IV collagen. Isolation, order and partial amino-acid sequence of cyanogen-bromide and tryptic peptides of pepsin fragment P1 from the alpha 1(IV) chain. Schuppan, D., Glanville, R.W., Timpl, R. Eur. J. Biochem. (1982) [Pubmed]
  10. A method for the evaluation of 3-hydroxyproline in the urine. Szymanovicz, A., Poulin, G., Randoux, A., Borel, J.P. Clin. Chim. Acta (1979) [Pubmed]
  11. Attaching human fibroblasts secrete a type I procollagen rich in 3-hydroxyproline. Schwartz, C.E., Hellerqvist, C.G., Cunningham, L.W. Biochem. Biophys. Res. Commun. (1979) [Pubmed]
  12. Prolyl 3-hydroxylase: partial characterization of the enzyme from rat kidney cortex. Risteli, J., Tryggvason, K., Kivirikko, K.I. Eur. J. Biochem. (1977) [Pubmed]
  13. Age-related changes in the composition of proteins in the trabecular meshwork of the human eye. Horstmann, H.J., Rohen, J.W., Sames, K. Mech. Ageing Dev. (1983) [Pubmed]
  14. Preparation of cell-free extracellular matrix from human peripheral nerve. Johnson, P.C., Duhamel, R.C., Meezan, E., Brendel, K. Muscle Nerve (1982) [Pubmed]
  15. Composition of the glomerular basement membrane in the congenital nephrotic syndrome of the Finnish type. Tryggvason, K. Eur. J. Clin. Invest. (1977) [Pubmed]
  16. Variations in chemical composition of human glomerular and tubular basement membranes with age and disease. Langeveld, J.P., Veerkamp, J.H., Monnens, L.A. Renal physiology. (1980) [Pubmed]
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