公开(公告)号：US07569130B2

公开(公告)日：2009-08-04

申请号：US10248526

申请日：2003-01-27

申请人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

发明人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

IPC分类号： G01N27/26

CPC分类号： G01N33/6827

摘要： The mechanism of the UV light-induced reaction between the indole moiety of tryptophan and chloroform, and the structure of the modified tryptophan and polypeptides including such modified tryptophan residues. The excited indole moiety, which is formed upon UV light irradiation, emits a solvated electron which initiates a series of events that yield fluorescent derivatives that have CHO group covalently bound to the indole moiety. These derivatives are herein referred to as formyltryptophan, and are relatively stable. Similar reactions are observed when 5-hydroxytryptophan, 5-fluorotryptophan, or N-methylindolacetate are used in place of tryptophan, or when other haloalkanes, such as trichloracetic acid, trichlorethanol, trichlorethane, bromoform, and iodoactetate are used in place of chloroform. The derivatives can be used in a variety of applications in fluorescence spectroscopy, and for nuclear magnetic resonance, X-ray crystallography, infra-red spectroscopy, circular dicroism and mass spectroscopy. Additionally, the UV light-induced reaction between the indole moiety of tryptophan and haloalkanes can be used to prepare derivatives of tryptophan for chemical cross-linking studies of proteins and peptides.

摘要翻译： 色氨酸和氯仿的吲哚部分之间的UV光诱导反应的机理，以及修饰的色氨酸和多肽的结构，包括这些修饰的色氨酸残基。 在UV光照射下形成的激发的吲哚部分发射溶剂化电子，其引发一系列事件，其产生具有与吲哚部分共价结合的CHO基团的荧光衍生物。 这些衍生物在本文中称为甲酰色氨酸，并且相对稳定。 当使用5-羟色氨酸，5-氟色氨酸或N-甲基吲哚乙酸乙酯代替色氨酸时，或当使用其它卤代烷烃如三氯乙酸，三氯乙醇，三氯乙烷，溴仿和碘代酸酯代替氯仿时，可以观察到类似的反应。 衍生物可用于荧光光谱学，核磁共振，X射线晶体学，红外光谱，圆形微球和质谱等多种应用。 此外，色氨酸和卤代烷烃的吲哚部分之间的紫外光诱导反应可用于制备色氨酸的衍生物用于蛋白质和肽的化学交联研究。

公开(公告)号：US08007646B2

公开(公告)日：2011-08-30

申请号：US12505859

申请日：2009-07-20

申请人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

发明人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

IPC分类号： G01N27/453

CPC分类号： G01N33/6827

摘要： The mechanism of the UV light-induced reaction between the indole moiety of tryptophan and chloroform, and the structure of the modified tryptophan and polypeptides including such modified tryptophan residues. The excited indole moiety, which is formed upon UV light irradiation, emits a solvated electron which initiates a series of events that yield fluorescent derivatives that have CHO group covalently bound to the indole moiety. These derivatives are herein referred to as formyltryptophan, and are relatively stable. Similar reactions are observed when 5-hydroxytryptophan, 5-fluorotryptophan, or N-methylindolacetate are used in place of tryptophan, or when other haloalkanes, such as trichloracetic acid, trichlorethanol, trichlorethane, bromoform, and iodoactetate are used in place of chloroform. The derivatives can be used in a variety of applications in fluorescence spectroscopy, and for nuclear magnetic resonance, X-ray crystallography, infra-red spectroscopy, circular dicroism and mass spectroscopy. Additionally, the UV light-induced reaction between the indole moiety of tryptophan and haloalkanes can be used to prepare derivatives of tryptophan for chemical cross-linking studies of proteins and peptides.

摘要翻译： 色氨酸和氯仿的吲哚部分之间的UV光诱导反应的机理，以及修饰的色氨酸和多肽的结构，包括这些修饰的色氨酸残基。 在UV光照射下形成的激发的吲哚部分发射溶剂化电子，其引发一系列事件，其产生具有与吲哚部分共价结合的CHO基团的荧光衍生物。 这些衍生物在本文中称为甲酰色氨酸，并且相对稳定。 当使用5-羟色氨酸，5-氟色氨酸或N-甲基吲哚乙酸乙酯代替色氨酸时，或当使用其它卤代烷烃如三氯乙酸，三氯乙醇，三氯乙烷，溴仿和碘代酸酯代替氯仿时，可以观察到类似的反应。 衍生物可用于荧光光谱学，核磁共振，X射线晶体学，红外光谱，圆形微球和质谱等多种应用。 此外，色氨酸和卤代烷烃的吲哚部分之间的紫外光诱导反应可用于制备色氨酸的衍生物用于蛋白质和肽的化学交联研究。

公开(公告)号：US20100089753A1

公开(公告)日：2010-04-15

申请号：US12505859

申请日：2009-07-20

申请人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

发明人： Robert A. Edwards ,  Raymond J. Turner ,  Carol Ladner ,  Jean Starkey ,  Eric Larson ,  Dmitri Kazmin

IPC分类号： C07K1/26 ,  G01N33/559

CPC分类号： G01N33/6827

摘要： The mechanism of the UV light-induced reaction between the indole moiety of tryptophan and chloroform, and the structure of the modified tryptophan and polypeptides including such modified tryptophan residues. The excited indole moiety, which is formed upon UV light irradiation, emits a solvated electron which initiates a series of events that yield fluorescent derivatives that have CHO group covalently bound to the indole moiety. These derivatives are herein referred to as formyltryptophan, and are relatively stable. Similar reactions are observed when 5-hydroxytryptophan, 5-fluorotryptophan, or N-methylindolacetate are used in place of tryptophan, or when other haloalkanes, such as trichloracetic acid, trichlorethanol, trichlorethane, bromoform, and iodoactetate are used in place of chloroform. The derivatives can be used in a variety of applications in fluorescence spectroscopy, and for nuclear magnetic resonance, X-ray crystallography, infra-red spectroscopy, circular dicroism and mass spectroscopy. Additionally, the UV light-induced reaction between the indole moiety of tryptophan and haloalkanes can be used to prepare derivatives of tryptophan for chemical cross-linking studies of proteins and peptides.

摘要翻译： 色氨酸和氯仿的吲哚部分之间的UV光诱导反应的机理，以及修饰的色氨酸和多肽的结构，包括这些修饰的色氨酸残基。 在UV光照射下形成的激发的吲哚部分发射溶剂化电子，其引发一系列事件，其产生具有与吲哚部分共价结合的CHO基团的荧光衍生物。 这些衍生物在本文中称为甲酰色氨酸，并且相对稳定。 当使用5-羟色氨酸，5-氟色氨酸或N-甲基吲哚乙酸乙酯代替色氨酸时，或当使用其它卤代烷烃如三氯乙酸，三氯乙醇，三氯乙烷，溴仿和碘代酸酯代替氯仿时，可以观察到类似的反应。 衍生物可用于荧光光谱学，核磁共振，X射线晶体学，红外光谱，圆形微球和质谱等多种应用。 此外，色氨酸和卤代烷烃的吲哚部分之间的紫外光诱导反应可用于制备色氨酸的衍生物用于蛋白质和肽的化学交联研究。