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    • 6. 发明授权
    • Azobenzene derivatives as labeling agents and intermediates thereof
    • 偶氮苯衍生物作为标记试剂及其中间体
    • US06602987B1
    • 2003-08-05
    • US09831494
    • 2001-08-07
    • Meir WilchekEdward A. BayerHeike HofstetterMargherita Morpurgo
    • Meir WilchekEdward A. BayerHeike HofstetterMargherita Morpurgo
    • C07K1706
    • C07D207/404C07C235/34C07C243/34C07C245/08C07C271/20C07C271/22C07C281/02C07D207/452G01N33/532G01N33/533
    • A compound of the formula I: wherein R is H or —N═N-2-carboxyphenyl; A is (CH2)n or —CH═CH—, wherein n is an integer from 0 to 10, or A may also be —CH(COOH)— when R is —N═N-2-carboxyphenyl; and X is a radical selected from the group consisting of: (i) Cl; (ii) COOR1, wherein R1 is p-nitrophenyl or N-succinimidyl; (iii) CONH—NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl; (iv) CONH—[B]—NHR3, wherein R3 is H, COOR1, or CO—[B′]—maleimido, wherein R1 is t-butyl, p-nitrophenyl or N-succinimidyl, and B and B′, the same or different, are (CH2)n wherein n is an integer from 2 to 10; (v) CONH—[B]—COOR4, wherein R4 is H, C1-C8 alkyl, N-succinimidyl; (vi) CONH—[B]—OH; (vii) CONH—[B]—CONH—NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl; and (viii) NHR2, wherein R2 is H, COO(t-butyl) or COObenzyl, when A is —CH(COOH)— and R is —N═N-2-carboxyphenyl. The 4′-hydroxyazobenzene-2-carboxylic acid (HABA) compounds are novel reagents for labeling, isolation and detection of biological molecules.
    • 式I的化合物:其中R是H或-N = N-2-羧基苯基; A是(CH 2)n或-CH = CH-,其中n是0至10的整数,或当R是-N = N-2-羧基苯基时,A也可以是-CH(COOH) 并且X是选自以下的基团:(i)Cl; (ii)COOR1,其中R1是对硝基苯基或N-琥珀酰亚胺基; (iii)CONH-NHR2,其中R2是H,COO(叔丁基)或COO苄基; (iv)CONH- [B] -NHR 3,其中R 3是H,COOR 1或CO- [B'] - 马来酰亚氨基,其中R 1是叔丁基,对硝基苯基或N-琥珀酰亚胺基,B和B' 相同或不同,为(CH 2)n,其中n为2至10的整数; (v)CONH- [B] -COOR 4,其中R 4是H,C 1 -C 8烷基,N-琥珀酰亚胺基; (vi)CONH- [B] -OH; (vii)CONH- [B] -CONH-NHR2,其中R2是H,COO(叔丁基)或COO苄基; 和(viii)当A为-CH(COOH) - 且R为-N = N-2-羧基苯基时,R 2为H,COO(叔丁基)或COO苄基的NHR 2。 4'-羟基偶氮苯-2-羧酸(HABA)化合物是生物分子标记,分离和检测的新型试剂。
    • 7. 发明授权
    • Modified avidin and streptavidin molecules and use thereof
    • 修饰的抗生物素蛋白和链霉亲和素分子及其用途
    • US5973124A
    • 1999-10-26
    • US973970
    • 1998-03-05
    • Edward A. BayerMeir WilchekEly Morag
    • Edward A. BayerMeir WilchekEly Morag
    • C12Q1/68B01J20/281C07K14/36C07K14/465C12N11/02G01N30/88G01N33/53G01N33/531G01N33/543C07K14/77G01N33/532
    • G01N33/54353C07K14/36C07K14/465C12N11/02G01N33/531
    • Biotin-binding modified avidin-type molecules are provided in which the essential tyrosine residue in the biotin-binding site is modified in such a way that its pKa is decreased in comparison to the pKa of the unmodified tyrosine residue in the corresponding unmodified avidin-type molecule. The avidin-type molecules include: (i) native egg-white avidin; (ii) recombinant avidin; (iii) deglycosylated forms of avidin; (iv) bacterial streptavidin; (v) recombinant streptavidin; (vi) truncated streptavidin; and (vii) derivatives of (i)-(vi) which are modified at sites other than the essential tyrosine residue. The modification is achieved by substitution at one or both ortho positions to the hydroxy radical of the tyrosine residue by radicals such as nitro, halogen, azo and amino. The modified avidin-type molecules can be used in all applications of the avidin-biotin technology.
    • PCT No.PCT / IL96 / 00014 Sec。 371日期:1998年3月5日 102(e)1998年3月5日PCT PCT 1996年6月13日PCT公布。 公开号WO97 / 00329 日期1997年1月3日提供了生物素结合修饰的抗生物素蛋白型分子,其中生物素结合位点中的必需酪氨酸残基被修饰,使得其pKa与未修饰的酪氨酸残基的pKa相比降低 相应的未修饰的抗生物素蛋白型分子。 抗生物素蛋白型分子包括:(i)天然蛋白抗生物素蛋白; (ii)重组抗生物素蛋白; (iii)去糖基化形式的抗生物素蛋白; (iv)细菌链霉抗生物素蛋白; (v)重组链霉亲和素; (vi)截短的链霉抗生物素蛋白; 和(vii)(i) - (vi)的衍生物,其在除必需酪氨酸残基之外的位点被修饰。 通过在硝基,卤素,偶氮和氨基等自由基的酪氨酸残基的羟基的一个或两个邻位进行取代来实现修饰。 修饰的抗生物素蛋白型分子可用于抗生物素蛋白 - 生物素技术的所有应用。