Org Lett. 2003 Aug 7;5(16):2817-20.

Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki reaction.

Source

Department of Chemistry, University of California, Irvine, California 92697-2025, USA.

Abstract

[reaction: see text] Since peroxidase-catalyzed dityrosine formation is inefficient for peptides, we have developed alternative conditions for intermolecular dityrosine formation using the Miyaura-Suzuki reaction. A one-pot reaction is effective for cross-linking short peptides, but longer peptides inhibit the Suzuki step, mandating a traditional two-step procedure using potassium acetate for the Miyaura reaction and potassium carbonate for the Suzuki coupling. These palladium-based methods are complementary to the well-established peroxidase-catalyzed oxidative phenolic coupling of full-length proteins.

PMID:: 12889882; [PubMed - indexed for MEDLINE]

Publication Types, MeSH Terms, Substances, Grant Support

Publication Types

Research Support, U.S. Gov't, P.H.S.

MeSH Terms

Substances

Grant Support

LinkOut - more resources

Full Text Sources

Other Literature Sources

COS Scholar Universe

Molecular Biology Databases

L-TYROSINE - HSDB

Supplemental Content

Save items

Related citations in PubMed

Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine. [J Org Chem. 2005]
Synthesis of the side chain cross-linked tyrosine oligomers dityrosine, trityrosine, and pulcherosine.
Skaff O, Jolliffe KA, Hutton CA. J Org Chem. 2005 Sep 2; 70(18):7353-63.
Dityrosine cross-linked Abeta peptides: fibrillar beta-structure in Abeta(1-40) is conducive to formation of dityrosine cross-links but a dityrosine cross-link in Abeta(8-14) does not induce beta-structure. [Chem Res Toxicol. 2003]
Dityrosine cross-linked Abeta peptides: fibrillar beta-structure in Abeta(1-40) is conducive to formation of dityrosine cross-links but a dityrosine cross-link in Abeta(8-14) does not induce beta-structure.
Yoburn JC, Tian W, Brower JO, Nowick JS, Glabe CG, Van Vranken DL. Chem Res Toxicol. 2003 Apr; 16(4):531-5.
Arylation of Phe and Tyr side chains of unprotected peptides by a Suzuki-Miyaura reaction in water. [Org Lett. 2008]
Arylation of Phe and Tyr side chains of unprotected peptides by a Suzuki-Miyaura reaction in water.
Vilaró M, Arsequell G, Valencia G, Ballesteros A, Barluenga J. Org Lett. 2008 Aug 7; 10(15):3243-5. Epub 2008 Jul 4.
Review Dityrosine as a product of oxidative stress and fluorescent probe. [Amino Acids. 2003]
Review Dityrosine as a product of oxidative stress and fluorescent probe.
Malencik DA, Anderson SR. Amino Acids. 2003 Dec; 25(3-4):233-47. Epub 2003 Aug 21.
Review The redox chemistry of the Alzheimer's disease amyloid beta peptide. [Biochim Biophys Acta. 2007]
Review The redox chemistry of the Alzheimer's disease amyloid beta peptide.
Smith DG, Cappai R, Barnham KJ. Biochim Biophys Acta. 2007 Aug; 1768(8):1976-90. Epub 2007 Feb 9.

See reviews... See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki rea...
Synthesis of dityrosine cross-linked peptide dimers using the Miyaura-Suzuki reaction.
Org Lett. 2003 Aug 7 ;5(16):2817-20.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: