Conjugates of an oligonucleotide/electronic conductor polymer wi

Details Conjugates of an oligonucleotide/electronic conductor polymer wi Conjugates of an oligonucleotide/electronic conductor polymer wi

1998-12-21

2000-12-12

Riley, Jezia

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 221, 536 241, 530402, 435 5, 435 6, C07H 2102, C07H 1900, C07K 100, C07K 1400, C07K 1600

Patent

active

061601039

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel methods and novel compounds for controlling the attachment of different molecules of interest to an electronically conductive polymer (ECP);
The application PCT WO 94/22889 in the name of CIS BIO INTERNATIONAL (inventors, TEOULE et al.) describes the attachment of oligonucleotides to a support which consists of an electronically conductive polymer (ECP).
This attachment can be effected in a variety of ways: is by chemically reacting the oligonucleotide on the previously functionalized ECP or by copolymerizing ECP monomers with the product of the condensation of the oligonucleotide on one of the said monomers). nucleotide or one oligonucleotide which has already been attached to the ECP using, for example, one of the standard methods for synthesizing nucleic acids.
The attachment of oligonucleotides to ECPs facilitates the isolation and use of oligonucleotide matrices which can, in particular, be employed for sequencing nucleic acids and for diagnosis.
Just like oligonucleotide matrices, peptide matrices and, more generally, matrices of various molecules represent a particularly advantageous tool, for example in the field of diagnosis or for screening active molecules. It would therefore be desirable for other types of matrix to be able to benefit from the improvements brought about by using ECPs.
However, the attachment of molecules of interest other than oligonucleotides, for example the attachment of peptides, to an ECP poses more problems than does the attachment of oligonucleotides.
Thus, although methods for synthesizing pyrrole carrying an amino acid or a dipeptide are described in the literature [GARNIER et al. J. Am. Chem. Soc., 116, 8813-8814 (1994)], these are methods for carrying out synthesis in solution, which methods do not in practice enable synthetic peptide molecules of a size greater than 2 or 3 amino acids to be obtained in sufficient yield. However, molecules which are of real interest within the field of diagnosis or that of screening active molecules are longer; for example, a "minimal" antigenic motif generally contains an average of 6 amino acids.
The usual methods of synthesizing peptides on a solid support, which methods are derived from the MERRIFIELD technique, involve the use of different groups for protecting the side chains of the amino acids. The elimination of these groups, and the separation of the peptide and support at the conclusion of the synthesis are effected in strong acid medium (hydrofluoric acid or trifluoroacetic acid). However, ECP monomers, in particular the pyrrole residue, have a tendency to polymerize in acid medium, thereby creating undesirable by-products.
It seems, therefore, that neither the synthesis method which is carried out in solution, and whose possibilities are limited to synthesizing dipeptides or tripeptides, nor synthesis on a support, whose implementation requires chemical conditions which are incompatible with the stability of the pyrrole residue, are suitable for synthesizing peptides which are modified by a pyrrole residue.
It is nevertheless possible to graft an ECP monomer, for example a pyrrole residue, onto a preformed oligopeptide which has been obtained by traditional peptide synthesis on a solid phase. This grafting can be effected using known methods, for example by reaction between a carboxylic derivative of the pyrrole (activated by a coupling reagent) and one of the available amino functions of a peptide (for example the amino function at the N-terminal end), in accordance with the following scheme [S. E. WOLOWACZ et al., Anal. Chem., 64, 1541-1545, (1992)]. Pyrrole--COOR+NH2--peptide.fwdarw.Pyrrole--CONH--peptide
At the conclusion of the reaction, the pyrrole-peptide conjugate has to be isolated from the reaction mixture containing the unreacted peptide and pyrrole as well as any possible salts and by-products.
The various methods which it might therefore be possible, a priori, to envisage using for this purpose are those which are customarily employed for purifying peptides, in particula

REFERENCES:
Solomons "Organic Chemistry, Fifth Edition" John Wiley and sons, Inc. pp. 997-1000, 1992

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