Pulcherosine | CAS#126723-16-8 | trimer

MedKoo Cat#: 145505 | Name: Pulcherosine

Description:

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

Pulcherosine is composed of isodityrosine and tyrosine oxidatively coupled via a biphenyl linkage such that the aromatic core is 2,2'-dihydroxy-3-phenoxybiphenyl. Pulcherosine can act as an intermediate in the conversion of isodityrosine to the tetramer, di-isodityrosine. Pulcherosine forms inter-polypeptide cross-links and/or wide intra-polypeptide loops.

Chemical Structure

Pulcherosine

CAS#126723-16-8

Theoretical Analysis

MedKoo Cat#: 145505

Name: Pulcherosine

CAS#: 126723-16-8

Chemical Formula: C27H29N3O9

Exact Mass: 539.1900

Molecular Weight: 539.54

Elemental Analysis: C, 60.11; H, 5.42; N, 7.79; O, 26.69

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Pulcherosine;

IUPAC/Chemical Name

(2S,2'S)-3,3'-(5-(4-((S)-2-amino-2-carboxyethyl)phenoxy)-6,6'-dihydroxy-[1,1'-biphenyl]-3,3'-diyl)bis(2-aminopropanoic acid)

InChi Key

YLKSMWKXSSBSNR-ACRUOGEOSA-N

InChi Code

1S/C27H29N3O9/c28-19(25(33)34)9-13-1-4-16(5-2-13)39-23-12-15(11-21(30)27(37)38)8-18(24(23)32)17-7-14(3-6-22(17)31)10-20(29)26(35)36/h1-8,12,19-21,31-32H,9-11,28-30H2,(H,33,34)(H,35,36)(H,37,38)/t19-,20-,21-/m0/s1

SMILES Code

N[C@@H](CC1=CC=C(OC2=CC(C[C@H](N)C(O)=O)=CC(=C2O)C3=CC(C[C@H](N)C(O)=O)=CC=C3O)C=C1)C(O)=O

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 539.54 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.

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: 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. doi: 10.1016/s0031-9422(97)00592-x. PMID: 9433813. 2: Nomura K, Suzuki N, Matsumoto S. Pulcherosine, a novel tyrosine-derived, trivalent cross-linking amino acid from the fertilization envelope of sea urchin embryo. Biochemistry. 1990 May 15;29(19):4525-34. doi: 10.1021/bi00471a004. PMID: 2372536. 3: Skaff O, Jolliffe KA, Hutton CA. Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine. J Org Chem. 2005 Sep 2;70(18):7353-63. doi: 10.1021/jo051076m. PMID: 16122259. 4: 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. doi: 10.1074/jbc.271.33.19950. PMID: 8702710. 5: Han KK, Martinage A. Post-translational chemical modifications of proteins-- III. Current developments in analytical procedures of identification and quantitation of post-translational chemically modified amino acid(s) and its derivatives. Int J Biochem. 1993 Jul;25(7):957-70. doi: 10.1016/0020-711x(93)90108-q. PMID: 8365549. 6: Choudhary P, Saha P, Ray T, Tang Y, Yang D, Cannon MC. EXTENSIN18 is required for full male fertility as well as normal vegetative growth in Arabidopsis. Front Plant Sci. 2015 Jul 22;6:553. doi: 10.3389/fpls.2015.00553. PMID: 26257758; PMCID: PMC4510346. 7: 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. PMID: 25536327; PMCID: PMC4275275. 8: Wu W, Chen Y, Hazen SL. Eosinophil peroxidase nitrates protein tyrosyl residues. Implications for oxidative damage by nitrating intermediates in eosinophilic inflammatory disorders. J Biol Chem. 1999 Sep 3;274(36):25933-44. doi: 10.1074/jbc.274.36.25933. PMID: 10464338. 9: Nomura K, Suzuki N. Sea urchin ovoperoxidase: solubilization and isolation from the fertilization envelope, some structural and functional properties, and degradation by hatching enzyme. Arch Biochem Biophys. 1995 Jun 1;319(2):525-34. doi: 10.1006/abbi.1995.1327. PMID: 7786038.