PREPARATION OF 5-(AMINOMETHYL)FLUORESCEIN AND 6-(AMINOMETHYL)FLUORESCEIN

被引:27
作者
MATTINGLY, PG
机构
[1] Abbott Laboratories, Diagnostics Division, Abbott Park, Illinois 60064, One Abbott Park Road
关键词
D O I
10.1021/bc00017a013
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
5(6)-Carboxyfluorescein is protected as the diacetate then reduced to 5(6)-(hydroxymethyl)fluorescein diacetate. The separated isomers are subjected to a Mitsunobu reaction with dibenzyl imidodicarbonate, yielding diprotected 5-and 6-(aminomethyl)fluorescein diacetate. Methanolysis of the acetates followed by deprotection with HBr/acetic acid gives 5- and 6-(aminomethyl)fluorescein hydrobromide.
引用
收藏
页码:430 / 431
页数:2
相关论文
共 13 条
[1]  
Brown, 1972, BORANES ORGANIC CHEM
[2]   CARBOXYFLUORESCEIN FLUOROCHROMASIA ASSAYS .1. NON-RADIOACTIVELY LABELED CELL-MEDIATED LYMPHOLYSIS [J].
BRUNING, JW ;
KARDOL, MJ ;
ARENTZEN, R .
JOURNAL OF IMMUNOLOGICAL METHODS, 1980, 33 (01) :33-44
[3]  
BYRNES PJ, 1988, Patent No. 279213
[4]   POLAR FLUORESCEIN DERIVATIVES AS IMPROVED SUBSTRATE PROBES FOR FLOW CYTOENZYMOLOGICAL ASSAY OF CELLULAR ESTERASES [J].
DIVE, C ;
COX, H ;
WATSON, JV ;
WORKMAN, P .
MOLECULAR AND CELLULAR PROBES, 1988, 2 (02) :131-145
[5]  
FINO JR, 1987, ANAL BIOCHEM, V162, P89
[6]   CHARACTERISTICS OF FLUOROPROBES FOR MEASURING INTRACELLULAR PH [J].
GRABER, ML ;
DILILLO, DC ;
FRIEDMAN, BL ;
PASTORIZAMUNOZ, E .
ANALYTICAL BIOCHEMISTRY, 1986, 156 (01) :202-212
[7]  
GREHN L, 1988, SYNTHESIS-STUTTGART, P992
[8]   REDUCTION OF ORGANIC-COMPOUNDS WITH DIBORANE [J].
LANE, CF .
CHEMICAL REVIEWS, 1976, 76 (06) :773-799
[9]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[10]   Fluorescein and some of its derivatives [J].
Orndorff, WR ;
Hemmer, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1927, 49 :1272-1280