Publications by authors named "Miriyala Bruhaspathy"

5 Publications

  • Page 1 of 1

Fluorous methods for the synthesis of peptides and oligonucleotides.

Top Curr Chem 2012 ;308:105-33

Department of Chemistry, Chevron Science Center, University of Pittsburgh, Pittsburgh, PA 15260, USA.

The non-covalent affinity of a perfluoro chain towards similar has been exploited by many to separate fluorous tagged compounds from non-fluorous compounds by F-SPE or F-LLE. This purification strategy found its application across diverse fields including peptide and oligonucleotide synthesis where even slight inefficient couplings result in deletion sequences that are often difficult to remove from the target sequence. Two commonly employed strategies to address this problem involve end-tagging the target sequence or capping the deletion sequences with fluorous tags. Solution phase syntheses using soluble fluorous supports are easier and quicker. These approaches are reviewed here in detail.
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http://dx.doi.org/10.1007/128_2011_247DOI Listing
August 2012

Fluorous synthesis of substituted sclerotigenin library.

J Comb Chem 2010 Jan-Feb;12(1):125-8

Fluorous Technologies, Inc., Pittsburgh, Pennsylvania 15238, USA.

A fluorous linker-assisted synthetic protocol has been developed for preparation of sclerotigenin-type benzodiazepine-quinazolinone library containing 144 analogues. Amide coupling of fluorous trimethoxybenzyl (TMB)-protected amino esters with anthranilic acids followed by base-promoted cyclizations afforded 4-benzodiazepine-2,5-diones. Further derivatization of benzodiazepinediones by reacting with azidobenzoyl chlorides, cyclization, and fluorous linker cleavage afforded the desired compound library. The reaction intermediates were purified by fluorous solid-phase extraction (F-SPE) and final products were further purified by prep-HPLC.
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http://dx.doi.org/10.1021/cc9001636DOI Listing
March 2010

Design, synthesis and activity of novel derivatives of oxybutynin and tolterodine.

Bioorg Med Chem Lett 2005 Apr;15(8):2093-6

Ranbaxy Research Laboratories, New Drug Discovery Research, Department of Medicinal Chemistry, Gurgaon 122 001, Haryana, India.

Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented.
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http://dx.doi.org/10.1016/j.bmcl.2005.02.036DOI Listing
April 2005

Hydroxylation of 10-deoxoartemisinin by Cunninghamella elegans.

J Nat Prod 2004 Sep;67(9):1595-7

Department of Medicinal Chemistry, University of Mississippi, University, Mississippi 38677-1848, USA.

The microbial metabolism of 10-deoxoartemisinin (1), a derivative of the antimalarial drug artemisinin, was investigated. Various strains of fungi were investigated for their ability to transform 1. Of these microorganisms, only Cunninghamella elegans was capable of transforming 1 to 5beta-hydroxy-10-deoxoartemisinin (2), 4alpha-hydroxy-1,10-deoxoartemisinin (3), and 7beta-hydroxy-10-deoxoartemisinin (4). The metabolites 2 and 4 retained an intact peroxide group and are therefore useful scaffolds for synthetic modification in the search for new antimalarial agents.
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http://dx.doi.org/10.1021/np040089cDOI Listing
September 2004

Hydroxylation of 10-deoxoartemisinin to 15-hydroxy-10-deoxoartemisinin by Aspergillus niger.

Biotechnol Lett 2004 Apr;26(7):607-10

Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, University, MS 38677-1848, USA.

The microbial hydroxylation of 10-deoxoartemisinin was investigated with the aim of obtaining preparative yields of hydroxy derivatives. During 14 d at 28 degrees C and pH 6.5 Aspergillus niger transformed 10-deoxoartemisinin (500 mg l(-1)) to 15-hydroxy-10-deoxoartemisinin (26%) and 7beta-hydroxy-10-deoxoartemisinin (69%).
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http://dx.doi.org/10.1023/b:bile.0000021965.55420.e9DOI Listing
April 2004