Galactosylhydroxylysine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 597511

CAS#: 32448-36-5

Description: Galactosylhydroxylysine residues present in bone type I collagen are terminal degradation products of the bone matrix that are released during bone resorption and excreted in the urine. 5-(galactosylhydroxy)-L-Lysine levels are elevated in patients with metabolic bone loss and thus may serve as a biochemical marker of bone collagen quality.


Price and Availability

Size
Price

5mg
USD 450
Size
Price

10mg
USD 850
Size
Price

Galactosylhydroxylysine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597511
Name: Galactosylhydroxylysine
CAS#: 32448-36-5
Chemical Formula: C12H24N2O8
Exact Mass: 324.1533
Molecular Weight: 324.33
Elemental Analysis: C, 44.44; H, 7.46; N, 8.64; O, 39.46


Synonym: Galactosylhydroxylysine; Hydroxylysine-galactose;

IUPAC/Chemical Name: (2S)-2,6-diamino-5-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanoic acid

InChi Key: OWGKYELXGFKIHH-ODPZDSJBSA-N

InChi Code: InChI=1S/C12H24N2O8/c13-3-5(1-2-6(14)11(19)20)21-12-10(18)9(17)8(16)7(4-15)22-12/h5-10,12,15-18H,1-4,13-14H2,(H,19,20)/t5?,6-,7+,8-,9-,10+,12+/m0/s1

SMILES Code: N[C@@H](CCC(O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)CN)C(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
2934.99.90.01


References

1: Sricholpech M, Perdivara I, Nagaoka H, Yokoyama M, Tomer KB, Yamauchi M. Lysyl hydroxylase 3 glucosylates galactosylhydroxylysine residues in type I collagen in osteoblast culture. J Biol Chem. 2011 Mar 18;286(11):8846-56. doi: 10.1074/jbc.M110.178509. Epub 2011 Jan 10. PubMed PMID: 21220425; PubMed Central PMCID: PMC3058983.

2: Leigh SD, Ju HS, Lundgard R, Daniloff GY, Liu V. Development of an immunoassay for urinary galactosylhydroxylysine. J Immunol Methods. 1998 Nov 1;220(1-2):169-78. PubMed PMID: 9839938.

3: Smith DF. Preparative scale isolation of galactosylhydroxylysine. Anal Biochem. 1976 Mar;71(1):106-13. PubMed PMID: 1275223.

4: Marabini R, Sirtori P, Chionna R, Barzizza L, Rubinacci A. Galactosylhydroxylysine and pyridinium cross links in monitoring the bone response to hormone replacement therapy. J Endocrinol Invest. 1996 Mar;19(3):154-8. PubMed PMID: 8743280.

5: LoCascio V, Braga V, Bertoldo F, Bettica P, Pasini AF, Stefani L, Moro L. Effect of bisphosphonate therapy and parathyroidectomy on the urinary excretion of galactosylhydroxylysine in primary hyperparathyroidism. Clin Endocrinol (Oxf). 1994 Jul;41(1):47-51. PubMed PMID: 8050131.

6: Isemura M, Ikenaka T, Mega T, Matsushima Y. On the structure of galactosylhydroxylysine and glycopeptides derived from bovine tracheal cartilage. Biochem Biophys Res Commun. 1974 Apr 8;57(3):751-7. PubMed PMID: 4857147.

7: Perdivara I, Perera L, Sricholpech M, Terajima M, Pleshko N, Yamauchi M, Tomer KB. Unusual fragmentation pathways in collagen glycopeptides. J Am Soc Mass Spectrom. 2013 Jul;24(7):1072-81. doi: 10.1007/s13361-013-0624-y. Epub 2013 Apr 30. PubMed PMID: 23633013; PubMed Central PMCID: PMC3679267.

8: Henkel W, Buddecke E. Purification and properties of UDP-glucose galactosylhydroxylysine collagen glucosyltransferase (EC 2.4.1.?) from bovine arterial tissue. Hoppe Seylers Z Physiol Chem. 1975 Jun;356(6):921-8. PubMed PMID: 241697.

9: Sricholpech M, Perdivara I, Yokoyama M, Nagaoka H, Terajima M, Tomer KB, Yamauchi M. Lysyl hydroxylase 3-mediated glucosylation in type I collagen: molecular loci and biological significance. J Biol Chem. 2012 Jun 29;287(27):22998-3009. doi: 10.1074/jbc.M112.343954. Epub 2012 May 9. PubMed PMID: 22573318; PubMed Central PMCID: PMC3391079.

10: Schröder CH, Langeveld JP, van Raay-Selten BH, Trijbels FJ, de Graaf R, Veerkamp JH, Monnens LA. Urinary excretion of hydroxylysine and its glycosides in normal persons of different ages--influence of maturation. Int J Pediatr Nephrol. 1985 Oct-Dec;6(4):239-44. PubMed PMID: 2419268.

11: Taga Y, Kusubata M, Ogawa-Goto K, Hattori S. Development of a novel method for analyzing collagen O-glycosylations by hydrazide chemistry. Mol Cell Proteomics. 2012 Jun;11(6):M111.010397. doi: 10.1074/mcp.M111.010397. Epub 2012 Jan 13. PubMed PMID: 22247541; PubMed Central PMCID: PMC3433922.

12: Grazioli V, Alfano M, Stenico A, Casari E. Urinary output of hydroxylysine glycosides and pyridinium cross-links in detecting rat bone collagen turnover rate. FEBS Lett. 1996 Jun 17;388(2-3):134-8. PubMed PMID: 8690072.

13: Kelleher PC. Urinary excretion of hydroxyproline, hydroxylysine and hydroxylysine glycosides by patients with Paget's disease of bone and carcinoma with metastases in bone. Clin Chim Acta. 1979 Mar 15;92(3):373-9. PubMed PMID: 436278.

14: Myllylä R, Wang C, Heikkinen J, Juffer A, Lampela O, Risteli M, Ruotsalainen H, Salo A, Sipilä L. Expanding the lysyl hydroxylase toolbox: new insights into the localization and activities of lysyl hydroxylase 3 (LH3). J Cell Physiol. 2007 Aug;212(2):323-9. Review. PubMed PMID: 17516569.

15: Plebani M, Bernardi D, Meneghetti MF, Ujka F, Zaninotto M. Biological variability in assessing the clinical value of biochemical markers of bone turnover. Clin Chim Acta. 2000 Sep;299(1-2):77-86. PubMed PMID: 10900294.

16: Schröder CH, Monnens LA, van Lith-Zanders HM, Trijbels JM, Veerkamp JH, Langeveld JP. Urinary excretion of hydroxylysine and its glycosides in Alport's syndrome and several other glomerulopathies. Nephron. 1986;44(2):103-7. PubMed PMID: 3774073.

17: Risteli M, Ruotsalainen H, Bergmann U, Venkatraman Girija U, Wallis R, Myllylä R. Lysyl hydroxylase 3 modifies lysine residues to facilitate oligomerization of mannan-binding lectin. PLoS One. 2014 Nov 24;9(11):e113498. doi: 10.1371/journal.pone.0113498. eCollection 2014. PubMed PMID: 25419660; PubMed Central PMCID: PMC4242627.

18: Moro L, Noris-Suarez K, Michalsky M, Romanello M, de Bernard B. The glycosides of hydroxylysine are final products of collagen degradation in humans. Biochim Biophys Acta. 1993 Mar 21;1156(3):288-90. PubMed PMID: 8461318.

19: Hamazaki H. Purification and characterization of a human lectin specific for penultimate galactose residues. J Biol Chem. 1986 Apr 25;261(12):5455-9. PubMed PMID: 3957931.

20: Schröder CH, Monnens LA, van Lith-Zanders HM, Trijbels JM, Veerkamp JH. The urinary excretion of total hydroxylysine and its glycosides in normal persons, and in patients suffering from Alport's syndrome--contribution of the peptide-bound fraction. Nephron. 1987;47(4):253-7. PubMed PMID: 3696326.