DIARYLSULFIDE BACKBONE CONTAINING PHOTOLABILE PROTECTING GROUPS

1 . A compound of the formula

wherein Y is S or O, and

A is selected from the group consisting of —CH 2 —, —CH 2 —CH 2 —, —CH(CH 3 )—, —CH(CH 3 )—CH 2 —, and

R1 is an unsubstituted or substituted aryl- or heteroaryl-group, and R3 is H, a methyl group or an ethyl group, and

wherein R2 is H, forms a phosphoramidite, H-phosphonate or phosphate triester, or

wherein R2 is

or wherein R2 is

wherein R4 is H, forms a phosphoramidite, H-phosphonate or phosphate triester, and

wherein R5 is H, OH, a halogen or XR6, wherein X is O or S and R6 is H, an alkyl-group, aryl-group, or OR6 forms a phosphoramidite, phosphodiester, phosphotriester, H-phosphonate or an acetal or silicone moiety, and

wherein B is selected from the group consisting of adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurine-9-yl, hypoxanthin-9-yl, 5-methylcytosinyl-1-yl, 5-amino-4-imidazolecarboxylic acid-1-yl or 5-amino-4-imidazolecarboxylic acid amide-3-yl, wherein when B is adenine, cytosine or guanine the primary amino group optionally has a protecting group or when B is thymine or uracil at the O 4 position is optionally a protecting group, or

wherein R 2 is

wherein R7 is a natural amino acid, a non-natural amino acid or an amino acid derivative forming an urethan bond to formula Ib, or

wherein formula IV represents the carboxy function of a natural amino acid, a non-natural amino acid or an amino acid derivative, forming an ester bond to formula Ib.

2 . The compound according to claim 1 wherein R1 is a phenyl-group, a tert-butyl-phenyl group, a 1- or 2-naphthyl-group, a 2-pyridyl-group an aminophenyl-group, an N-alkylaminophenyl-group, an N-Acylaminophenyl-group, a carboxyphenyl-group, a phenylcarboxylic ester or an amide.

3 . The compound according to claim 1 wherein A is —CH(CH 3 )—CH 2 —.

4 . The compound according to claim 1 wherein R2 is a phosphoramidite or —P(OCH 2 CH 2 CN)(N-iPr 2 ).

5 . The compound according to claim 1 wherein R3 is H or an ethyl group.

6 . The compound according to claim 1 wherein R4 is H and R5 is H.

7 . The compound according to claim 1 wherein B is selected from the group consisting of adenine, cytosine, guanine, thymine or uracil.

8 . The compound according to claim 1 wherein when B is adenine, cytosine or guanine the protecting group is phenoxyacetyl-, 4-tert-butyl-phenoxyacetyl-, 4-isopropyl-phenoxyacetyl- or dimethylformamidino-residues, when B is adenine the protecting group is benzoyl- or p-nitro-phenyl-ethoxy-carbonyl-(p-NPPOC)-residues, when B is guanine the protecting group is isobutyroyl-, p-nitrophenylethyl (p-NPE) or p-NPEOC-residues and when B is cytosine the protecting group is benzoyl-, isobutyryl- or p-NPEOC-residues.

9 . The compound according to claim 1 wherein R7 is a natural amino acid.

10 . A method for preparing a diarylsulfide backbone containing one or more photolabile protecting group(s) according to claim 1 comprising the steps of

a) Provision of p-diethylbenzene as a starting material;

b) Bromination of the phenylring;

c) Nitration of the obtained compound in Nitric- and Sulfuric Acid in the position para- to the Bromine;

d) Purification and crystallization;

e) Hydroxymethylation of the compound at the benzylic position;

f) Conversion of the aromatic bromine group to the arylsulfide using thiophenol;

g) Purification;

h) Conversion of the alcohol to chlorocarbonate; and

i) Reaction of the chlorocarbonate with a nucleoside and reaction of the nucleoside with a phosphitylating agent, or

Reaction of the chlorocarbonate with an amino acid derivative.

11 . The method according to claim 10 , characterized in that R1 is a phenyl-group, a tert-butyl-phenyl group, a 1- or 2-naphthyl-group or a 2-pyridyl-group.

12 . The method according to claim 10 , characterized in that A is —CH(CH 3 )—CH 2 —.

13 . The method according to claim 10 , characterized in that R3 is H or an ethyl group.

14 . A method of forming an array through photolithography, said method comprising contacting a substrate having a site activated by exposure to light with a compound of claim 1 .

15 . The method of claim 14 wherein R 2 is

wherein R7 is a natural amino acid, a non-natural amino acid or an amino acid derivative forming an urethan bond to formula Ib, or

wherein formula IV represents the carboxy function of a natural amino acid, a non-natural amino acid or an amino acid derivative, forming an ester bond to formula Ib.

16 . The method of claim 14 wherein the contacting of the substrate with a compound of claim 1 produces a DNA microarray or a peptide microarray.

17 . The method of claim 16 wherein the method produces a DNA microarray.

18 . The method of claim 16 wherein the method produces a peptide microarray.

19 . The method of claim 14 wherein the substrate and/or the compound is activated by exposure to light between the wavelengths of 374 to 405 nm.