Glucosylgalactosylhydroxylysine

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

MedKoo CAT#: 597510

CAS#: 32448-35-4

Description: Glucosylgalactosylhydroxylysine is a bone formation and bone resorption marker that is related to bone turnover processes during growth and development as well as metabolic bone diseases; it is also involved with reactions associated with the functional expression of human mannan-binding proteins (MBPs) in human cell lines transfected with MBP cDNA.

Chemical Structure

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Glucosylgalactosylhydroxylysine
CAS# 32448-35-4
Instruction

Theoretical Analysis

MedKoo Cat#: 597510
Name: Glucosylgalactosylhydroxylysine
CAS#: 32448-35-4
Chemical Formula: C18H34N2O13
Exact Mass: 486.21
Molecular Weight: 486.470
Elemental Analysis: C, 44.44; H, 7.05; N, 5.76; O, 42.75

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Glucosylgalactosylhydroxylysine; Hydroxylysine-glucose-galactose;

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

InChi Key: UTIRJVJBKWSIOX-ZTPIPZIISA-N

InChi Code: InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12-,13-,14+,15+,17+,18+/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[C@@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 486.47 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Hamazaki H, Hamazaki MH. Catalytic site of human protein-glucosylgalactosylhydroxylysine glucosidase: Three crucial carboxyl residues were determined by cloning and site-directed mutagenesis. Biochem Biophys Res Commun. 2016 Jan 15;469(3):357-62. doi: 10.1016/j.bbrc.2015.12.005. Epub 2015 Dec 9. PubMed PMID: 26682924.

2: Colley KJ, Baenziger JU. Identification of the post-translational modifications of the core-specific lectin. The core-specific lectin contains hydroxyproline, hydroxylysine, and glucosylgalactosylhydroxylysine residues. J Biol Chem. 1987 Jul 25;262(21):10290-5. PubMed PMID: 3611062.

3: Katzman RL, Halford MH, Reinhold VN, Jeanloz RW. Isolation and structure determination of glucosylgalactosylhydroxylysine from sponge and sea anemone collagen. Biochemistry. 1972 Mar 28;11(7):1161-7. PubMed PMID: 4401167.

4: 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.

5: 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.

6: Savolainen ER, Kero M, Pihlajaniemi T, Kivirikko KI. Deficiency of galactosylhydroxylysyl glucosyltransferase, an enzyme of collagen synthesis, in a family with dominant epidermolysis bullosa simplex. N Engl J Med. 1981 Jan 22;304(4):197-204. PubMed PMID: 6449670.

7: 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.

8: 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.

9: 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.

10: Takuwa A, Yoshida T, Maruno T, Kawahara K, Mochizuki M, Nishiuchi Y, Kobayashi Y, Ohkubo T. Ordered self-assembly of the collagenous domain of adiponectin with noncovalent interactions via glycosylated lysine residues. FEBS Lett. 2016 Jan;590(2):195-201. doi: 10.1002/1873-3468.12034. Epub 2016 Jan 28. PubMed PMID: 26823167.

11: 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.

12: Pecile A, Netti C, Sibilia V, Villa I, Calori G, Tenni R, Coluzzi M, Moro GL, Rubinacci A. Comparison between urinary pyridinium cross-links and hydroxylysine glycosides in monitoring the effects of ovariectomy and 17 beta-estradiol replacement in aged rats. J Endocrinol. 1996 Sep;150(3):383-90. PubMed PMID: 8882157.

13: 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.

14: 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.

15: Terajima M, Perdivara I, Sricholpech M, Deguchi Y, Pleshko N, Tomer KB, Yamauchi M. Glycosylation and cross-linking in bone type I collagen. J Biol Chem. 2014 Aug 15;289(33):22636-47. doi: 10.1074/jbc.M113.528513. Epub 2014 Jun 23. PubMed PMID: 24958722; PubMed Central PMCID: PMC4132771.

16: Allevi P, Anastasia M, Paroni R, Ragusa A. The first synthesis of glucosylgalactosyl hydroxylysine (Glu-Gal-Hyl), an important biological indicator of collagen turnover. Bioorg Med Chem Lett. 2004 Jun 21;14(12):3319-21. PubMed PMID: 15149698.

17: 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.

18: 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.

19: Pearson CH, Ainsworth L, Chovelon A. The determination of small amounts of collagen hydroxylysyl glycosides. Connect Tissue Res. 1978;6(1):51-9. PubMed PMID: 149649.

20: Bisbee WC, Kelleher PC. A method for measuring hydroxylysine and glycosylated hydroxylysines in urine and protein hydrolysates. Clin Chim Acta. 1978 Nov 15;90(1):29-36. PubMed PMID: 719889.