MedKoo Cat#: 597511 | Name: Galactosylhydroxylysine

Description:

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

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.

Chemical Structure

Galactosylhydroxylysine
Galactosylhydroxylysine
CAS#32448-36-5

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

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
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
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).
HS Tariff Code
2934.99.9001
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 324.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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.