CONVERSION OF HYDROXYPROLINE TO PYRROLE-2-CARBOXYLIC ACID
نویسندگان
چکیده
منابع مشابه
Conversion of hydroxyproline to pyrrole-2-carboxylic acid.
Although studies on the degradative metabolism of hydroxyproline have revealed that this amino acid is converted at least in part to glutamic acid (I-G), knowledge of the intermediates in this conversion and of other products of hydroxyproline metabolism is not yet complete. In the course of experiments on the metabolism of hydroxyproline, it was observed that incubation of hydroxyproline with ...
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In the title compound, C(5)H(5)NO(2), the pyrrole ring and its carboxyl substituent are close to coplanar, with a dihedral angle of 11.7 (3)° between the planes. In the crystal structure, adjacent mol-ecules are linked by pairs of O-H⋯O hydrogen bonds to form inversion dimers. Additional N-H⋯O hydrogen bonds link these dimers into chains extending along the a axis.
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The Grignard, Wittig, Tebbe, Horner-Emmons, and Reformatsky reactions of the 4-oxoproline esters gave the corresponding 4-alylated or 4-alkylidenated products, respectively. The products were properly treated with bases to cause aromatization, giving 4-substituted pyrrole-2-carboxylic acid esters such as methyl 4-methylpyrrole-2-carboxylate, which is a trail pheromone of Atta texana.
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The phenazine derivative 2-hydroxyphenazine (2-OH-PHZ) plays an important role in the biocontrol of plant diseases, and exhibits stronger bacteriostatic and fungistatic activity than phenazine-1-carboxylic acid (PCA) toward some pathogens. PhzO has been shown to be responsible for the conversion of PCA to 2-OH-PHZ, however the kinetics of the reaction have not been systematically studied. Furth...
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The crystal structure of the title compound, C(10)H(6)ClNO(2), can be described by two types of crossed layers which are parallel to (110) and (10). The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯N hydrogen bonds, resulting in the formation of a two-dimensional network and reinforcing the cohesion of the structure.
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ژورنال
عنوان ژورنال: Journal of Biological Chemistry
سال: 1957
ISSN: 0021-9258
DOI: 10.1016/s0021-9258(18)64854-9