scholarly journals Microbiological degradation of bile acids. Metabolites formed from 3-(3a α-hexahydro-7a β-methyl-1,5-dioxoindan-4 α-yl) propionic acid by Streptomyces rubescens

1977 ◽  
Vol 164 (3) ◽  
pp. 715-726 ◽  
Author(s):  
S Hashimoto ◽  
S Hayakawa
Keyword(s):  
Propionic Acid ◽  
Bond Formation ◽  
Amide Bond ◽  
Side Chain ◽  
Carbonyl Groups ◽  
Dioic Acid ◽  
Amide Bond Formation ◽  
Alpha Beta ◽  
Compound Ii ◽  
New Compounds

1. The metabolism of 3-(3a alpha-hexahydro-7a beta-methyl-1,5-dioxoindan-4 alpha-yl)propionic acid (III), which is a possible precursor of 2,3,4,6,6a beta, 7,8,9,9a alpha,9b beta-decahydro-6a beta-methyl-1H-cyclopenta[f]quinoline-3,7-dione (II) formed from cholic acid (I) by streptomyces rubescens, was investigated by using the same organism. 2. This organism effected amide bond formation, reduction of the carbonyl groups, trans alpha beta-desaturation and R-oriented beta-hydroxylation of the propionic acid side chain and skeleton cleavage, and the following metabolites were isolated as these forms or their derivatives: compound (II), 1,2,3,4 a beta,-5,6,6a beta,7,8,9a alpha,9b beta-dodecahydro-6a beta -methylcyclopental[f][1]benzopyran-3,7-dione (IVa), (1R)-1,2,3,4a beta,5,6,6a beta,7,8,9.9a alpha,9b beta-dodecahydro-1-hydroxy-6a beta-methylcyclopenta[f][1]benzopyran-3,7-dione (IVb), (E)-3-(3aalpha-hexahydro-5 alpha-hydroxy-7a beta-methyl-l-oxo-indan-4 alpha-yl)prop-2-enoic acid (V), (+)-(5R)-5-methyl-4-oxo-octane-1,8-dioic acid (VI), 3-(4-hydroxy-5-methyl-2-oxo-2H-pyran-6-yl)propionic acid (VII) and 3-(3a alpha-hexahydro-1 beta-hydroxy-7a beta-methyl-5-oxoindan-4 alpha-yl)propionic acid (VIII). The metabolites (IVb), (V), (VI) and (VII) were new compounds, and their structures were established by chemical synthesis. 3. The question of whether these metabolites are true degradative intermediates is discussed, and a degradative pathway of compound (III) to the possible precursor of compound (VII), 7-carboxy-4-methyl-3,5-dioxoheptanoyl-CoA (IX), is tentatively proposed. The further degradation of compound (IX) to small fragments is also considered.

scholarly journals Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens

1976 ◽  
Vol 160 (3) ◽  
pp. 745-755 ◽  
Author(s):  
S Hayakawa ◽  
S Hashimoto ◽  
T Onaka
Keyword(s):  
Cholic Acid ◽  
Bond Formation ◽  
Valeric Acid ◽  
Amide Bond ◽  
Side Chain ◽  
Mechanism Of Formation ◽  
Partial Synthesis ◽  
Degradative Pathway ◽  
Amide Bond Formation ◽  
New Compounds

The metabolism of cholic acid (I) by Streptomyces rubescens was investigated. This organism effected ring A cleavage, side-chain shortening and amide bond formation and gave the following metabolites: (4R)-4-[4α-(2-carboxyethyl)-3aα-hexahydro-7aβ-methyl-5-oxoindan-1 β-yl]valeric acid (IIa) and its mono-amide (valeramide) (IIb); and 2,3,4,6, 6aβ,7,8,9,9aα,9bβ-decahydro-6aβ-methyl-1H-cyclopenta[f]quinoline-3,7-dione(IIIe)and its homologues with the β-oriented side chains, valeric acid, valeramide, butanone and propionic acid, in the place of the oxo group at C-7, i.e.compounds (IIIa), (IIIb), (IIIc) and (IIId) respectively. All the nitrogenous metabolites were new compounds, and their structures were established by partial synthesis except for the metabolite (IIIc). The mechanism of formation of these metabolites is considered. A degradative pathway of cholic acid (I) into the metabolites is also tentatively proposed.

Convenient amidation of carboxyl group of carboxyphenylboronic acids

2016 ◽  
Vol 0 (0) ◽  
Author(s):  
Julia Nowak-Jary
Keyword(s):  
Bond Formation ◽  
Amide Bond ◽  
Protecting Groups ◽  
Nucleophilic Attack ◽  
Carboxyl Groups ◽  
Coupling Reagents ◽  
Mild Conditions ◽  
Amide Bond Formation ◽  
One Step ◽  
New Compounds

AbstractThe use of catalysts in the activation of carboxyl groups towards nucleophilic attack and the protection of other functional groups by suitable protecting groups are standard and necessary procedures in amide bond formation. In contrast to the usual methods, various new compounds, amides of APTES ((3-aminopropyl)triethoxysilane, 3-triethoxysilylpropylamine) and carboxyphenylboronic acids, as well as the amides of aniline and carboxyphenylboronic acids, were obtained in good yields by a one-step synthesis under mild conditions without using any coupling reagents or additional catalysts.

Peptide synthesis by prior thiol capture. 4. Amide bond formation. The effect of a side-chain substituent on the rates of intramolecular O,N-acyl transfer

1986 ◽  
Vol 51 (17) ◽  
pp. 3320-3324 ◽  
Author(s):  
D. S. Kemp ◽  
Nicholas G. Galakatos ◽  
Stanley Dranginis ◽  
Christopher Ashton ◽  
Nader Fotouhi ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Acyl Transfer ◽  
Side Chain ◽  
Amide Bond Formation

Diethylphosphoryl-OxymaB (DEPO-B) as a Solid Coupling Reagent for Amide Bond Formation

2018 ◽  
Vol 16 (1) ◽  
pp. 30-33
Author(s):  
Ashish Kumar ◽  
Yahya E. Jad ◽  
Ayman El-Faham ◽  
Beatriz G. de la Torre ◽  
Fernando Albericio
Keyword(s):  
Bond Formation ◽  
Hydrolytic Stability ◽  
Solid Material ◽  
Amide Bond ◽  
Amide Bond Formation ◽  
Coupling Reagent

A new phosphonium based coupling reagent DEPO-B has been synthesized from 5- (hydroxyimino)-1,3-dimethylpyrimidine-2,4,6 (1H,3H,5H)-trione (Oxyma B) and diethyl chlorophosphate in presence of base. It is a solid material and the hydrolytic stability and solubility was evaluated for confirming its capability for usage in automated peptide synthesizer.

A Review of Amide Bond Formation in Microwave Organic Synthesis

2014 ◽  
Vol 11 (4) ◽  
pp. 592-604 ◽  
Author(s):  
Natalia Lukasik ◽  
Ewa Wagner-Wysiecka
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Amide Bond ◽  
Amide Bond Formation

A computational study on the mechanism of ynamide-mediated amide bond formation from carboxylic acids and amines

2017 ◽  
Vol 15 (30) ◽  
pp. 6367-6374 ◽  
Author(s):  
Song-Lin Zhang ◽  
Hai-Xing Wan ◽  
Zhu-Qin Deng
Keyword(s):  
Reaction Mechanism ◽  
Carboxylic Acids ◽  
Computational Study ◽  
Bond Formation ◽  
Amide Bond ◽  
Reactivity Pattern ◽  
Amide Bond Formation ◽  
Coupling Reagent ◽  
Catalytic Effects ◽  
Acid Substrate

A detailed computational study is presented on the reaction mechanism of ynamide-mediated condensation of carboxylic acids with amines to produce amides, which elucidates the reactivity pattern of the coupling reagent ynamide and discloses crucial bifunctional catalytic effects of the carboxylic acid substrate during aminolysis.

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