Solid phase organic synthesis

Details Solid phase organic synthesis Solid phase organic synthesis

1998-05-29

2002-12-10

Venkat, Jyothsna (Department: 1627)

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Enzymatic production of a protein or polypeptide

C435S007100, C436S501000, C436S518000, C525S054200, C530S300000, C530S333000, C530S334000, C530S335000, C530S322000

Reexamination Certificate

active

06492136

ABSTRACT:

This application claims the benefit of Great Britain Patent Application No. 95 25007.2, filed Dec. 7, 1995, and Great Britain Patent Application No. 96 13921.7 filed Jul. 3, 1996.
This invention relates to solid phase organic synthesis; more particularly, it relates to the use of certain linkers between reactant and support, which may be cleaved as desired by exo-enzymes.
As will be explained in more detail below, the present invention provides a method of synthesis of a material corresponding to the following general formula:
R
3
—X—H
characterised in that it comprises a material corresponding to the following general formula:
being cleaved as indicated enzymatically or non-enzymatically using acid catalysis in the presence of a nucleophile;
wherein
R
1
represents a group providing the site for exo-enzyme or acid hydrolysis;
R
2
represents an optional intermediate linked to a solid support;
R
3
represents a residue of a carbohydrate, (oligo-)saccharide, (glyco-)peptide, (glyco-) lipid or of an organic molecule which is heterocyclic and/or aromatic;
X represents O, N(H), N(R″), C(O)O, S, C(O)N(H) or C(O)N(R″), R″ being a non-interfering substituent; and
Support represents a solid support.
Preferably R
1
represents: monosaccharide, phosphate, sulphate, —NH—CO—CH
2
—Ph,
wherein
x represents an integer; and
R
5
and R
6
each represents a non-interfering group.
Preferably, R
2
represents:
Preferably R
3
represents a residue of a (glyco-)peptide or (oligo-)saccharide.
Preferably, X represents O, N(H), N(R″), C(O)O, C(O)N(H) or S.
Preferably Support represents “EUPERGIT”, amino-“TENTAGEL”, “PEGA” resin or aminopropyl silica.
For the present purposes, the preferred exo-enzyme is penicillin amidase.
The present invention also relates to the use of an exo-linker in a solid phase organic synthesis.
The present invention further relates to a reagent corresponding to the formula:


REFERENCES:
patent: 4659774 (1987-04-01), Webb et al.
patent: 5679769 (1997-10-01), Danishefsky et al.
Liang et al. “Parallel Synthesis and Screening . . . ”, Science, vol. 274, pp. 1520-1522, Nov. 1996.*
Dineva et al. “Phenylacetyl Group as Enzyme-Cleavable . . . ”, Bioorg. Med. Chem. Lett., vol. 3, No. 12, pp. 2781-2784, Dec. 1993.*
Hoffman, et al. “A New Safty-Catch Peptide-Resin Linkage For The Direct Release of Peptides into Aqueous Buffer,”Tetrahedron Letters, 35: 7763-7766 (1994).
Hoffman, et al. “A Facile Preparation of N-(Isopropxyalkyl) Amides by Generation and Trapping of N-Acyliminium Ions from Ionization-Rearrangement Reactions of N-Triflyloxy Amides,”Journal of Organic Chemistry, 59: 3530-3539 (1994).
Elmore, et al. “An Enzyme-scissile Linker for Solid-phase Peptide Synthesis,”J. Chem. Soc., Chem. Commun., 14: 1033-1034 (1992).

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