PNA synthesis using a base-labile amino protecting group

Details PNA synthesis using a base-labile amino protecting group PNA synthesis using a base-labile amino protecting group

1997-10-29

2000-09-19

Lukton, David

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530300, 530332, 536 187, 536 253, 544264, C07K 104

Patent

active

061214183

ABSTRACT:
PNA synthesis using a base-labile amino protecting group Processes are described for preparing PNA oligomers, ##STR1## in which R.sup.0 is hydrogen, alkanoyl, alkoxycarbonyl, cycloalkanoyl, aroyl, heteroaroyl, or a group which favors the intracellular uptake of the oligomer, A and Q are amino acid residues, k and 1 are 0 to 20, n is 1-50, B is a nucleotide base which is customary in nucleotide chemistry, and Q.sup.0 is OH, NH.sub.2, or alkylamino which can be substituted by OH or NH.sub.2. In these processes, the amino acid residues and the structural components ##STR2## in which PG is a base-labile amino protecting group and B' is a nucleotide base which is protected on its exocyclic amino function, are coupled step-wise, in accordance with the solid-phase method, onto a polymeric support which is provided with an anchor group, and, after the construction is complete, the target compounds are cleaved from the polymeric support using a cleaving reagent. Intermediates of the PNA oligomers are also described, as are processes for their preparation.

REFERENCES:
patent: 5527675 (1996-06-01), Coull
patent: 5539082 (1996-07-01), Nielsen
patent: 5539083 (1996-07-01), Cook
Thomson, Tetrahedron 51, 6179, 1995.
Gross, The Peptides, vol. 3, pp. 21-24, 84-88, 223-229, 1981.
Michael Egholm et al., "Peptide Nucleic Acids (PNA) oligonucleotide Analogues With An Achiral Peptide Backbone," Journal of The Ameircan Chemical Society, vol. 114, No. 5, Feb. 1992, pp. 1895-1897.
Kim Dueholm et al., "Synthesis Of Peptide Nucleic Acid Monomers Containing The Four Natural Nucleobases: Thymine, Cytosine, Adenine, And Guanine And Their Oligomerization," vol. 59, No. 19, Sep. 1994, pp. 5767-5773. Journal of Organic Chemistry.
W.S. Saari et al, "Cyclization-Activated Prodrugs. Basic Esters of 5-Bromo-2' deoxyuridine," Journal Of Medicinal Chemistry, vol. 33, No. 9, pp. 2590-2595 (1990).
E.P. Heimer et al., "Synthesis Of Analogs and Oligomers of N-(2-amino-ethyl) Glycine and Their Gastrointestinal Absorption In The Rat," vol. 23, pp. 203-211 (1984).
Heimer et al., "Synthesis Of Analogs And Oligomers of N-(2-aminoethyl) glycine And Their Gastrointestinal Absorption In The Rat", Int. J. Peptide Protein Res. 23, (1984) pp. 203-211.
Hanvey, Science 258, 1481, 1992.
Barany, Int. J. Pept. Prot. Res. 30, 705, 1987.
Nielsen Science 254, 1497, 1991.

Affiliated with

Also associated with

Rating

PNA synthesis using a base-labile amino protecting group does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with PNA synthesis using a base-labile amino protecting group, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and PNA synthesis using a base-labile amino protecting group will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1074365