title: Synthesis of functionalised nucleosides for incorporation into nucleic acid-based serine protease mimics.
abstract: The synthesis of nucleosides modified with an extra imidazole, carboxyl and hydroxyl group is described. These nucleosides can be incorporated into an oligonucleotide duplex, thus generating a novel type of serine protease mimic.
authors: Ghent University, Department of Organic Chemistry, Laboratory for Organic and Biomimetic Chemistry, Krijgslaan 281 (S4), Gent, Belgium.
authors: Mieke A
authors: MA
authors: Catry
authors: Annemieke
authors: A
authors: Madder
mesh_terms: D002384:Catalysis; D020134:Catalytic Domain; D002918:Chymotrypsin / Q000737:chemistry / Q000378:metabolism; D006868:Hydrolysis; D007093:Imidazoles / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D018716:Molecular Mimicry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D017434:Protein Structure, Tertiary; D012697:Serine Endopeptidases / Q000737:chemistry* / Q000378:metabolism
chemical_list: D007093:Imidazoles; D009705:Nucleosides; D009841:Oligonucleotides; D010455:Peptides; C029899:imidazole; D012697:Serine Endopeptidases; D002918:Chymotrypsin; C117608:alpha-chymotrypsin
references: Appl Biochem Biotechnol. 1994 May-Jun;47(2-3):199-210; discussion 210-2
references: 7944338
references: Nature. 1969 Jan 25;221(5178):337-40
references: 5764436
references: Chem Rev. 2002 Dec;102(12):4501-24
references: 12475199
references: Bioconjug Chem. 2002 Mar-Apr;13(2):333-50
references: 11906272
references: J Mol Biol. 1969 Dec 14;46(2):337-48
references: 5360043
references: Angew Chem Int Ed Engl. 2001 Jul 16;40(14):2631-2635
references: 29712333
references: Proc Natl Acad Sci U S A. 1994 May 10;91(10):4110-4
references: 8183880
references: J Comb Chem. 2002 Nov-Dec;4(6):552-62
references: 12425599
references: Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1073-5
references: 14565347
references: Proc Natl Acad Sci U S A. 1993 Sep 1;90(17):8282-6
references: 8367494
references: Bioorg Med Chem. 2003 Aug 5;11(16):3499-511
references: 12878143
references: Science. 1990 Jun 22;248(4962):1544-7
references: 2360048
references: Nucleic Acids Res. 2004 Jul 23;32(13):3887-97
references: 15273275
references: J Comput Aided Mol Des. 1996 Feb;10(1):11-22
references: 8786411
references: Bioorg Med Chem. 2000 Dec;8(12):2675-80
references: 11131157
references: Angew Chem Int Ed Engl. 2000 Jan;39(1):145-148
references: 10649356
references: Chem Res Toxicol. 1997 Feb;10(2):165-71
references: 9049427
references: Bioorg Med Chem. 1996 Dec;4(12):2043-54
references: 9022970
references: J Org Chem. 1998 Apr 17;63(8):2548-2559
references: 11672118
references: Bioorg Med Chem Lett. 2002 Sep 2;12(17):2363-6
references: 12161134
references: Nature. 1967 May 13;214(5089):652-6
references: 6049071
references: J Org Chem. 1971 Jan 29;36(2):250-4
references: 5545352
references: Chem Res Toxicol. 1995 Sep;8(6):865-74
references: 7492736
references: Chem Rev. 2002 Jan;102(1):1-27
references: 11782127
references: Curr Protoc Nucleic Acid Chem. 2007 Dec;Chapter 4:Unit 4.22
references: 18428976
references: J Am Chem Soc. 2000 Mar 22;122(11):2433-9
references: 11543272
references: J Lipid Res. 1967 Mar;8(2):142-5
references: 14564721
references: Nucleic Acids Res. 2004 Feb 02;32(2):710-8
references: 14757835
references: Bioconjug Chem. 2000 Jul-Aug;11(4):599-603
references: 10898582
references: Org Biomol Chem. 2004 Oct 7;2(19):2793-7
references: 15455151
references: J Am Chem Soc. 2002 Aug 28;124(34):9960-1
references: 12188639
references: Proc Natl Acad Sci U S A. 1994 May 10;91(10):4106-9
references: 8183879
references: J Am Chem Soc. 2004 Dec 8;126(48):15642-3
references: 15571376