Organometallic iron, chromium and tungsten compds. R1A(CH2)nCHa[(CH2)mD(R5XYQ)p]b [1, a+b = 3, provided a<3 and at least in one branch m>0; p = 1, 2; n = 0-5, m = 0-8, preferably n = 0-2, m = 1; R1 = H, CO, CHO, C1-6 alkanedioic monoacyl, carboxyalkylamino, carboxy, carbamoyl, 1-imidazolecarbonyl; A, D = O, N, S; X = C0-5 alkylene, CO, carbamoyl, CO(CH2)1-5, C(O)S; Y = C0-5 alkylene,, (CH2)1-5NHCO, (CH2)1-5SCO; Q = (CO)3Cr(5-C6H5), C:Cr(CO)5, C:W(CO)5, (5-C5H4)Fe(5-C5H5); preferably Q = ferrocenyl, (CO)3Cr(5-C6H5)], useful as electrochem. and fluorescent markers for DNA and RNA bonding with peptide nucleic acids (PNA), were prepd. by stepwise modification of precursors A(CH2)nCHa[(CH2)mD]b with reagents R1-E and E1R5XYQ (E, E1 = leaving groups); or by esterification of A(CH2)nC[(CH2)mN(R5COOH)2]3, followed by amidation or thiolation and attachment of the required organometallic moiety. The prepd. mols. 1 were then bound to the biomols. PNA, DNA or RNA, preferably to PNA, suitably modified for peptide synthesis, mainly for the purposes of diagnostics. In an example, compd. H2NC(CH2OCH2Fc)3 (20; Fc = ferrocenyl) was prepd. by etherification of N-Cbz-tris(hydroxymethyl)methanamine with ferrocenemethanol and subsequent deprotection in 90% yield. In another example, tyrosine PNA monomer was modified by 20 giving 4'-[tris(ferrocenylmethoxymethyl)methyl]carbamoyl deriv. (30). These products are preferably used as labels of biomols. (for example: nucleic acids, oligonucleotides, PNAs, peptides, proteins, steroids etc.) mainly used in the field of diagnostics

Synthesis of organometallic derivatives and their use as fluorescent and electrochemical markers for peptide nucleic acids / S. Maiorana, C. Baldoli, C. Rigamonti, P.R. Mussini.

Synthesis of organometallic derivatives and their use as fluorescent and electrochemical markers for peptide nucleic acids

S. Maiorana
Primo
;
C. Rigamonti
Penultimo
;
P.R. Mussini
Ultimo
2006

Abstract

Organometallic iron, chromium and tungsten compds. R1A(CH2)nCHa[(CH2)mD(R5XYQ)p]b [1, a+b = 3, provided a<3 and at least in one branch m>0; p = 1, 2; n = 0-5, m = 0-8, preferably n = 0-2, m = 1; R1 = H, CO, CHO, C1-6 alkanedioic monoacyl, carboxyalkylamino, carboxy, carbamoyl, 1-imidazolecarbonyl; A, D = O, N, S; X = C0-5 alkylene, CO, carbamoyl, CO(CH2)1-5, C(O)S; Y = C0-5 alkylene,, (CH2)1-5NHCO, (CH2)1-5SCO; Q = (CO)3Cr(5-C6H5), C:Cr(CO)5, C:W(CO)5, (5-C5H4)Fe(5-C5H5); preferably Q = ferrocenyl, (CO)3Cr(5-C6H5)], useful as electrochem. and fluorescent markers for DNA and RNA bonding with peptide nucleic acids (PNA), were prepd. by stepwise modification of precursors A(CH2)nCHa[(CH2)mD]b with reagents R1-E and E1R5XYQ (E, E1 = leaving groups); or by esterification of A(CH2)nC[(CH2)mN(R5COOH)2]3, followed by amidation or thiolation and attachment of the required organometallic moiety. The prepd. mols. 1 were then bound to the biomols. PNA, DNA or RNA, preferably to PNA, suitably modified for peptide synthesis, mainly for the purposes of diagnostics. In an example, compd. H2NC(CH2OCH2Fc)3 (20; Fc = ferrocenyl) was prepd. by etherification of N-Cbz-tris(hydroxymethyl)methanamine with ferrocenemethanol and subsequent deprotection in 90% yield. In another example, tyrosine PNA monomer was modified by 20 giving 4'-[tris(ferrocenylmethoxymethyl)methyl]carbamoyl deriv. (30). These products are preferably used as labels of biomols. (for example: nucleic acids, oligonucleotides, PNAs, peptides, proteins, steroids etc.) mainly used in the field of diagnostics
Università degli Studi di Milano
WO2006006196
PCT/IT2005/000406
19-gen-2006
Settore CHIM/06 - Chimica Organica
Settore CHIM/01 - Chimica Analitica
http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=WO2006006196&F=0&QPN=WO2006006196
Synthesis of organometallic derivatives and their use as fluorescent and electrochemical markers for peptide nucleic acids / S. Maiorana, C. Baldoli, C. Rigamonti, P.R. Mussini.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/30166
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