Fluorescent dye intermediates

• US 5,625,081 A
• Filed: 01/13/1994
• Issued: 04/29/1997
• Est. Priority Date: 07/02/1986
• Status: Expired due to Fees

• Current Assignee: PerkinElmer Life Sciences, Inc.
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Trainor, George L.
• Primary Examiner(s): Houtteman, Scott W.
• Application Number:
  US08/181,284
• Time in Patent Office: 1,202 Days
• Field of Search: 536/25.34, 549/388, 549/392
• US Class Current: 549/392
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07F 9/6512 having the nitrogen atoms in positions 1 and 3
• CPC Class Codes: C07F 9/65586 at least one of the hetero rings does not contain nitrogen as ring hetero atom
• CPC Class Codes: C07F 9/6561 containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• CPC Class Codes: C07H 19/10 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C12Q 1/6869 Methods for sequencing
• CPC Class Codes: G01N 27/44721 by optical means
• CPC Class Codes: G01N 27/44726 using specific dyes, markers or binding molecules

Abstract

Intermediates for fluorescent dyes based on 9-carboxyethyl-6-hydroxy-3-oxo-3H-xanthene which are useful as reporters for reporter-labeled DNA fragments are described. The intermediates are protected fluorescent dyes bearing acyloxy groups at the 3 and 9 positions and an alkoxy group at the 9 position. Deprotection of the protected fluorescent dye by treatment with aqueous ammonia regenerates free dye.

Claims

1. A compound having the structure ##STR22## wherein n=2 or 3 and R₁ and R₂ are H, lower alkyl, halo, lower alkoxy, and cyano and R'"'"' is an alkyl or aryl group and R" is an alkyl group.

2. A compound having the structure ##STR23## wherein n=2 or 3 and R₁ and R₂ are H, lower alkyl, halo, lower alkoxy, and cyano, R'"'"' is an alkyl or aryl group, and R" is an alkyl group and X is a good leaving group.

3. A compound having the structure ##STR24## wherein n=2 or 3 and R₁ and R₂ are H, lower alkyl, halo, lower alkoxy, and cyano, R'"'"' is an alkyl or aryl group, and R" is an alkyl group and X is a good leaving group.

4. A compound having the structure ##STR25## wherein n=2 or 3 and R₁ and R₂ are H, lower alkyl, halo, lower alkoxy, and cyano and R'"'"' is an alkyl or aryl group and R" is an alkyl group and R₄ is H or a trivalent phosphorus moiety and B is a heterocyclic base.