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MedKoo Cat#: 598074 | Name: Isodityrosine

Description:

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

Isodityrosine is a new cross-linking amino acid from plant cell-wall glycoprotein.

Chemical Structure

Isodityrosine
Isodityrosine
CAS#83118-65-4

Theoretical Analysis

MedKoo Cat#: 598074

Name: Isodityrosine

CAS#: 83118-65-4

Chemical Formula: C18H20N2O6

Exact Mass: 360.1321

Molecular Weight: 360.36

Elemental Analysis: C, 59.99; H, 5.59; N, 7.77; O, 26.64

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
Isodityrosine;
IUPAC/Chemical Name
(2S)-2-amino-3-(4-(5-(2-amino-2-carboxyethyl)-2-hydroxyphenoxy)phenyl)propanoic acid
InChi Key
FWZXNPNHUWFOCM-LSLKUGRBSA-N
InChi Code
InChI=1S/C18H20N2O6/c19-13(17(22)23)7-10-1-4-12(5-2-10)26-16-9-11(3-6-15(16)21)8-14(20)18(24)25/h1-6,9,13-14,21H,7-8,19-20H2,(H,22,23)(H,24,25)/t13-,14?/m0/s1
SMILES Code
N[C@@H](CC1=CC=C(OC2=CC(CC(N)C(O)=O)=CC=C2O)C=C1)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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 360.36 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: Gupta A, Sen S, Harmata M, Pulley SR. Synthesis of (S,S)-isodityrosine by Dötz benzannulation. J Org Chem. 2005 Sep 2;70(18):7422-5. PubMed PMID: 16122268. 2: Fry SC. Isodityrosine, a new cross-linking amino acid from plant cell-wall glycoprotein. Biochem J. 1982 May 15;204(2):449-55. PubMed PMID: 7115340; PubMed Central PMCID: PMC1158371. 3: Held MA, Tan L, Kamyab A, Hare M, Shpak E, Kieliszewski MJ. Di-isodityrosine is the intermolecular cross-link of isodityrosine-rich extensin analogs cross-linked in vitro. J Biol Chem. 2004 Dec 31;279(53):55474-82. Epub 2004 Oct 1. PubMed PMID: 15465824. 4: Jung ME, Lazarova TI. New Efficient Method for the Total Synthesis of (S,S)-Isodityrosine from Natural Amino Acids. J Org Chem. 1999 Apr 30;64(9):2976-2977. PubMed PMID: 11674381. 5: Tan L, Pu Y, Pattathil S, Avci U, Qian J, Arter A, Chen L, Hahn MG, Ragauskas AJ, Kieliszewski MJ. Changes in cell wall properties coincide with overexpression of extensin fusion proteins in suspension cultured tobacco cells. PLoS One. 2014 Dec 23;9(12):e115906. doi: 10.1371/journal.pone.0115906. eCollection 2014. PubMed PMID: 25536327; PubMed Central PMCID: PMC4275275. 6: Brady JD, Fry SC. Formation of Di-Isodityrosine and Loss of Isodityrosine in the Cell Walls of Tomato Cell-Suspension Cultures Treated with Fungal Elicitors or H2O2. Plant Physiol. 1997 Sep;115(1):87-92. PubMed PMID: 12223793; PubMed Central PMCID: PMC158463. 7: Waffenschmidt S, Woessner JP, Beer K, Goodenough UW. Isodityrosine cross-linking mediates insolubilization of cell walls in Chlamydomonas. Plant Cell. 1993 Jul;5(7):809-20. PubMed PMID: 7689882; PubMed Central PMCID: PMC160318. 8: Jacob JS, Cistola DP, Hsu FF, Muzaffar S, Mueller DM, Hazen SL, Heinecke JW. Human phagocytes employ the myeloperoxidase-hydrogen peroxide system to synthesize dityrosine, trityrosine, pulcherosine, and isodityrosine by a tyrosyl radical-dependent pathway. J Biol Chem. 1996 Aug 16;271(33):19950-6. PubMed PMID: 8702710. 9: Brady JD, Sadler IH, Fry SC. Di-isodityrosine, a novel tetrametric derivative of tyrosine in plant cell wall proteins: a new potential cross-link. Biochem J. 1996 Apr 1;315 ( Pt 1):323-7. PubMed PMID: 8670125; PubMed Central PMCID: PMC1217189. 10: Brady JD, Sadler IH, Fry SC. Pulcherosine, an oxidatively coupled trimer of tyrosine in plant cell walls: its role in cross-link formation. Phytochemistry. 1998 Feb;47(3):349-53. PubMed PMID: 9433813. 11: Biggs KJ, Fry SC. Solubilization of covalently bound extensin from capsicum cell walls. Plant Physiol. 1990 Jan;92(1):197-204. PubMed PMID: 16667247; PubMed Central PMCID: PMC1062270. 12: Cooper JB, Varner JE. Cross-linking of soluble extensin in isolated cell walls. Plant Physiol. 1984 Oct;76(2):414-7. PubMed PMID: 16663856; PubMed Central PMCID: PMC1064302. 13: Cegelski L, O'Connor RD, Stueber D, Singh M, Poliks B, Schaefer J. Plant cell-wall cross-links by REDOR NMR spectroscopy. J Am Chem Soc. 2010 Nov 17;132(45):16052-7. doi: 10.1021/ja104827k. Epub 2010 Oct 21. PubMed PMID: 20964382. 14: Hitotsuyanagi Y, Miyazawa A, Hinosawa TA, Nakagawa Y, Hasuda T, Takeya K. Aza-cycloisodityrosine analogue of RA-VII, an antitumor bicyclic hexapeptide. Bioorg Med Chem Lett. 2013 Dec 15;23(24):6728-31. doi: 10.1016/j.bmcl.2013.10.033. Epub 2013 Oct 26. PubMed PMID: 24268554. 15: Hirsinger C, Parmentier Y, Durr A, Fleck J, Jamet E. Characterization of a tobacco extensin gene and regulation of its gene family in healthy plants and under various stress conditions. Plant Mol Biol. 1997 Jan;33(2):279-89. PubMed PMID: 9037146. 16: Yasuzawa T, Shirahata K, Sano H. K-13, a novel inhibitor of angiotensin I converting enzyme produced by Micromonospora halophytica subsp. exilisia. II. Structure determination. J Antibiot (Tokyo). 1987 Apr;40(4):455-8. PubMed PMID: 3034845. 17: Cai Q, He G, Ma D. Mild and nonracemizing conditions for Ullmann-type diaryl ether formation between aryl iodides and tyrosine derivatives. J Org Chem. 2006 Jul 7;71(14):5268-73. PubMed PMID: 16808515. 18: Ryden P, Selvendran RR. Cell-wall polysaccharides and glycoproteins of parenchymatous tissues of runner bean (Phaseolus coccineus). Biochem J. 1990 Jul 15;269(2):393-402. PubMed PMID: 2167068; PubMed Central PMCID: PMC1131590. 19: Cooper JB, Varner JE. Insolubilization of hydroxyproline-rich cell wall glycoprotein in aerated carrot root slices. Biochem Biophys Res Commun. 1983 Apr 15;112(1):161-7. PubMed PMID: 6838603. 20: Lardinois OM, Ortiz de Montellano PR. Intra- and intermolecular transfers of protein radicals in the reactions of sperm whale myoglobin with hydrogen peroxide. J Biol Chem. 2003 Sep 19;278(38):36214-26. Epub 2003 Jul 10. PubMed PMID: 12855712.