Scalable Synthesis of Lissamine Rhodamine B Sulfonyl Chloride and Incorporation of Xanthene Derivatives onto Polymer Supports

Hua Yang; Sundar Vasudevan; Christopher O. Oriakhi; Jay Shields; Rich G. Carter

doi:10.1055/s-2008-1032172

PAPER

Scalable Synthesis of Lissamine Rhodamine B Sulfonyl Chloride and Incorporation of Xanthene Derivatives onto Polymer Supports

Hua Yang^a, Sundar Vasudevan^b, Christopher O. Oriakhi^b, Jay Shields^b, Rich G. Carter*^a
^a Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR 97331, USA
Fax: +1(541)7379496; e-Mail: rich.carter@oregonstate.edu;
^b Hewlett-Packard Corporation, 1000 NE Circle Blvd, Corvallis, OR 97330, USA

Abstract

Alle Artikel dieser Rubrik

Abstract

A scalable synthetic route to lissamine rhodamine B sulfonyl chloride has been developed and a series of monomeric derivatives of this xanthene dye have been synthesized. Their subsequent incorporation into polymer supports has been accomplished and led to improved thermal stability for the conjugates as compared to the free dye.

Key words

heterocycles - polymers - dyes

Volltext

Referenzen

References

1a Thazhathveetil AK. Liu S.-T. Indig FE. Seidman MM. Bioconjugate Chem. 2007, 18: 431

1b Dagher R. Pigault C. Bonnet D. Boeglin D. Pourbaix C. Kilhoffer M.-C. Villa P. Wermuth CG. Hibert M. Haiech J. Biochim. Biophys. Acta 2006, 1763: 1250

1c Chan EWL. Yousaf MN. J. Am. Chem. Soc. 2006, 128: 15542

1d Lee JS. Lim H. Ha K. Cheong H. Yoon KB. Angew. Chem. Int. Ed. 2006, 45: 5292

1e Kumar S. Zhou B. Liang F. Yang H. Wang W.-Q. Zhang Z.-Y. J. Proteome Res. 2006, 5: 1898

1f Biskup MB. Müller JU. Weingart R. Schmidt RR. ChemBioChem 2005, 6: 1007

2a Pitner JB, and Hoke RA. inventors; US Patent 5302731.

2b Kang HC. inventors; US Patent 5846737.

2c Yamashita Y. inventors; JP 2004217524.

2d Lefevre C. Kang HC. Haugland RP. Malekzadeh N. Arttamangkul S. Haugland RP. Bioconjugate Chem. 1996, 7: 482

3

Acros Catalog Number 41323-0050. Pricing in 2006/2007 catalog: $407.90 for 5 grams.

4a Steingruber E. Endriss H. Winnacker-Küchler: Chemische Technik 5th ed., Vol. 7: Wiley-VCH; Weinheim: 2004. p.391

4b Gregory P. Chem. Ind. 1989, 679

5 Tarumoto N. Miyagawa N. Takahara S. Yamaoka T. J. Photopolym. Sci. Technol. 2005, 18: 673

6

Also called Food Red No. 106: TCI America catalog ^#F0144. 2006-2007 catalog price $66.95 for 25 grams.

7 Van Eeden J. Skowronska-Ptasinska M. Grootenhuis PDJ. Harkema S. Reinhoudt DN. J. Am. Chem. Soc. 1989, 111: 700

8 Snyder HR. Heckert RE. J. Am. Chem. Soc. 1952, 74: 2006

9 Blackburn C. Achab A. Elder A. Shosh S. Guo J. Harriman G. Jones M. J. Org. Chem. 2005, 70: 10206