Nucleoside derivatives with photolabile protective groups

US5763599A · kind A · utility

Assignee

• Wolfgang Pfleiderer · DE

Inventors

• Wolfgang Pfleiderer · Konstanz, DE
• Heiner Giegrich · Waldkraiburg, DE

Key dates

• Filing date: Aug 9, 1996
• Grant date: Jun 9, 1998
• Expiry date: Aug 9, 2016

Classification

• Technology area (CPC Y): Emerging Cross-Sectional Technologies
• CPC primary: Y02P20/55
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to nucleoside derivatives having photolabile protective groups of the general formula (I) ##STR1## in which R.sup.1 .dbd.H, NO.sub.2, CN, OCH.sub.3, halogen or alkyl or alkoxyalkyl having 1 to 4 C atoms PA1 R.sup.2 .dbd.H, OCH.sub.3 PA1 R.sup.3 .dbd.H, F, Cl, Br, NO.sub.2 PA1 R.sup.4 .dbd.H, halogen, OCH.sub.3, or an alkyl radical having 1 to 4 C atoms PA1 R.sup.5 .dbd.H or a usual functional group for preparing oligonucleotides PA1 R.sup.6 .dbd.H, OH, halogen or XR.sup.8, where X.dbd.O or S and R.sup.8 represents a protective group usual in nucleotide chemistry, PA1 B=adenine, cytosine, guanine, thymine, uracil, 2,6-diaminopurin-9-yl, hypoxanthin-9-yl, 5-methylcytosin-1-yl, 5-amino-4-imidazolcarboxamid-1-yl, or 5-amino-4-imidazolcarboxamid-3-yl, where in the case of B=adenine, cytosine or guanine, the primary amino function optionally exhibits a permanent protective group. These derivatives may be used for the light-controlled synthesis of oligonucleotides on a DNA chip.