Efficient fluorescein spirolactam and bis-spirolactam synthesis

被引:20
作者
Adamczyk, M [1 ]
Grote, J [1 ]
机构
[1] Abbott Labs, Div Diagnost, Dept Chem D9NM, Abbott Pk, IL 60064 USA
关键词
D O I
10.1081/SCC-100105396
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of fluorescein methyl ester at ambient temperature with a variety of amines containing different functional groups afforded a family of spirolactams, the structures of which were verified by MS, NMR, and x-ray crystallography. Bis-spirolactams were prepared by subsequent reaction of an aminospirolactam with another molecule of fluorescein methyl ester.
引用
收藏
页码:2681 / 2690
页数:10
相关论文
共 19 条
[1]   Resin-supported labeling reagents [J].
Adamczyk, M ;
Fishpaugh, JR ;
Mattingly, PG .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :217-220
[2]   O-(fluoresceinylmethyl)hydroxylamine (OFMHA):: A fluorescent reagent for detection of damaged nucleic acids [J].
Adamczyk, M ;
Mattingly, PG ;
Moore, JA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (24) :3599-3602
[3]   Chemoenzymatic synthesis of 3′-O-(carboxyalkyl)fluorescein labels [J].
Adamczyk, M ;
Grote, J ;
Moore, JA .
BIOCONJUGATE CHEMISTRY, 1999, 10 (03) :544-547
[4]   Synthesis of novel spirolactams by reaction of fluorescein methyl ester with amines [J].
Adamczyk, M ;
Grote, J .
TETRAHEDRON LETTERS, 2000, 41 (06) :807-809
[5]  
ANTHONI U, 1995, STRUCTURAL CHEM, V3, P161
[6]   COMPARISON OF 3 COMMON AMINE REACTIVE FLUORESCENT-PROBES USED FOR CONJUGATION TO BIOMOLECULES BY CAPILLARY ZONE ELECTROPHORESIS [J].
BANKS, PR ;
PAQUETTE, DM .
BIOCONJUGATE CHEMISTRY, 1995, 6 (04) :447-458
[7]   THE EFFECT OF FLUORESCEIN LABELS ON THE AFFINITY OF ANTISERA TO SMALL HAPTENS [J].
COLBERT, DL ;
EREMIN, SA ;
LANDON, J .
JOURNAL OF IMMUNOLOGICAL METHODS, 1991, 140 (02) :227-233
[8]   A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water [J].
Dujols, V ;
Ford, F ;
Czarnik, AW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7386-7387
[9]   On the phthalein of oxyhydroquinone. [J].
Feuerstein, W ;
Dutoit, M .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1901, 34 :2637-2642
[10]   Conformational analysis of phthalein derivatives acting as thymidylate synthase inhibitors by means of H-1 NMR and quantum chemical calculations [J].
Ghelli, S ;
Rastelli, G ;
Barlocco, D ;
Rinaldi, M ;
Tondi, D ;
Pecorari, P ;
Costi, MP .
BIOORGANIC & MEDICINAL CHEMISTRY, 1996, 4 (10) :1783-1794