Diarylsulfide backbone containing photolabile protecting groups

Patent metadata

Field	Value
Publication number	US-10150791-B2
Application number	US-201715425329-A
Country	US
Kind code	B2
Filing date	Feb 6, 2017
Priority date	Apr 7, 2011
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

Abstract

The present disclosure relates to photoactivable protecting groups containing a diarylsulfide chromophore, a method for the synthesis thereof and their use as photoactivable protecting groups using maskless photolithography based array synthesis.

First claim

What is claimed is:

1. A compound of the formula

wherein Y is S, 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

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.

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.

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

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

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

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

7. 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.

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

9. The compound of claim 1 wherein Y is S; A is —CH(CH 3 )CH 2 —; R1 is phenyl, tert-butyl-phenyl, 1- or 2-naphtyl or 2-pyridyl; and R3 is H or ethyl.

Assignees

• Roche Diagnostics Operations Inc

Inventors

• Stengele Klaus-Peter

Classifications

• C07H19/10

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• C07C319/14

  of sulfides · CPC title

• C07H19/20 Primary

  with the saccharide radical esterified by phosphoric or polyphosphoric acids · CPC title

• C07D213/70

  Sulfur atoms · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title