Indole propionic acid

Although tryptophan does not dissolve in benzene, 3-indole-propionic acid ester (ft =CH3 C6H13) is soluble in benzene, and converts smoothly to the corresponding 2 -formamidophenyl-... 

Levels of IAA were analyzed by HPLC with a fluorometric detector and indole-propionic acid as an internal standard. Levels of ABA were analyzed by GLC with an ECD and [14C]ABA as an internal standard. Means of results of 3 experiments and standard errors are given (n=3). Reproduced and revised with permission from ref. 8. 

Carboxy-3-indole)propionic acid refluxed 20 hrs. with a little KCN in acetic anhydride —5-keto-l,3,4,5-tetrahydrobenz[cd] indole. Y 80%. Other methods were not successful. (F. C. Uhle, Am. Soc. 71, 761 (1949).)... 

A solution of 143 mg p-(4-carboxy-3-indole)-propionic acid (0.6 mmol) and 15 mg potassium acetate (0.15 mmol) in 5 mL acetic anhydride was maintained at reflux temperature for 16 h. The acetic anhydride was distilled under reduced pressure. The residue was extracted with refluxing benzene. The solution was clarified by filtration and concentrated under diminished pressure. The remainder (125 mg) was recrystallized from a mixture of dichloromethane and ether to give 104 mg l-acetyl-5-keto-l,3,4,5-tetrahydrobenz(ed) indole, m.p. 120-140°C. Further recrystallization from a mixture of dichloromethane and ether gave 90 mg pure product, in a yield of 71%, m.p. 147-152°C. 

Method One, Snyder et al. (410, 741). Ethyl acetamidomalonate -)- gramine methiodide sodium - ethyl o-acetamido-o-carbethoxy-j3-(3-indole)-propionate (A) a-acetamido-a-carbmgr-jS-(3-indole)-propionic acid -> N-acetyltryptophan -> tryptophan (81% yield based on (A)]. 

Park YD, Rizzo TR, Peteanu LA, Levy DH (1986) Electronic spectroscopy of tryptophan analogs in supersonic jets - 3-indole acetic-acid, 3-indole propionic-acid, tryptamine, and N-acetyl tryptophan ethyl-ester. J Chem Phys 84(12) 6539-6549... 

Initially the modifier consisted of indole propionic acid dissolved in water at a concentration of 1 mM. Increasing the concentration of indole propionic acid up to the limit of its solubility increases the initial activity of the modified RNase. The use of modifiers such as 5-hydroxyindole-3-acetic acid and 5-hydroxyindole-3-acetamide, which are more water soluble than indole propionic acid, increased the activity even further. 

Carney, J.R., and T. Zwier. 2001. Conformational flexibility in small biomolecules Tryptamine and 3-indole-propionic acid. Chem. Phys. Lett. 341 77-85. 

Gruen and Nicholes (158) examined in detail the relative effectiveness of various additives in the 6N HCl hydrolysis of proteins. Acid hydrolysis was carried out in the presence of a reducing agent or a substituted indole compound such as tryptamine or 3-indole propionic acid, which lack the carboxyl or amino function, respectively, of tryptophan. The rationale was that these molecules would be degraded in preference to tryptophan. 

Purification of 2-(4 -[ I]iodo-biphenyl-4-sulfonylamino)-3-(l//-indol-3-yl)-propionic acid and 2-(4 -[ I]iodo-biphenyl-4-sulfonylamino)-3-(lff-indol-3-yl)-propionamide... 

Dissolve 2.75 g anhydrous sodium carbonate in a mixture of 50 ml acetic acid and 25 ml propionic acid. Add 11.7 g (0.1M) indole... 

The cyclocondensation of 3-aminopyrido[3,4-h]indole (1090) and EMME in boiling acetic acid and propionic acid for 8 hr or 4 hr gave pyrimido[2, 1 6,1 ]pyrido[3,4-b]indolecarboxylate(1091) in52%and65% yields, respectively [87MIP4, 87MIP5 881JC(B)484]. 

Fig. 8. Selected examples of aromatic donor molecules that form complexes with HRP C. The apparent dissociation constant for complex formation with the resting state plant enzyme is given (original references should be consulted for details of solution conditions and error estimations). (1) 2-Naphthohydroxamic acid (228) (2) benzhydroxamic acid (228) (3) 2-hydroxybenzhydroxamic acid (salicyUiydroxamic acid) (228) (4) benzhy-drazide (228) (5) cyclohexylhydroxamic acid (228) (6) 4-methylphenol (p-cresol) (192) (7) 2-methoxyphenol(guaiacol) (192) (8) indole-3-propionic acid(24i) (9)p-coumaric acid (238) (10) aniline (243).

Structural information on aromatic donor molecule binding was obtained initially by using H NMR relaxation measurements to give distances from the heme iron atom to protons of the bound molecule. For example, indole-3-propionic acid, a structural homologue of the plant hormone indole-3-acetic acid, was found to bind approximately 9-10 A from the heme iron atom and at a particular angle to the heme plane (234). The disadvantage of this method is that the orientation with respect to the polypeptide chain cannot be defined. Other donor molecules examined include 4-methylphenol (p-cresol) (235), 3-hydroxyphenol (resorcinol), 2-methoxy-4-methylphenol and benzhydroxamic acid (236), methyl 2-pyridyl sulfide and methylp-tolyl sulfide (237), and L-tyrosine and D-tyrosine (238). Distance constraints of between 8.4 and 12.0 A have been reported (235-238). Aromatic donor proton to heme iron distances of 6 A reported earlier for aminotriazole and 3-hydroxyphenol (resorcinol) are too short because of an inappropriate estimate of the molecular correlation time (239), a parameter required for the calculations. Distance information for a series of aromatic phenols and amines bound to Mn(III)-substituted HRP C has been published (240). 

Indometacin is an indole acetic acid derivative, while naproxen is a propionic acid derivative. Both are non-steroidal anti-inflammatory drugs (NSAIDs). Indometacin is associated with a higher incidence of side-effects, particularly gastrointestinal as well as headache and dizziness. 

Beccalli et al. reported a new synthesis of staurosporinone (293) from 3-cyano-3-(lH-indol-3-yl)-2-oxo propionic acid ethyl ester (1464) (790). The reaction of 1464 with ethyl chlorocarbonate and triethylamine afforded the compound 1465, which, on treatment with dimethylamine, led to the corresponding hydroxy derivative 1466. The triflate 1467 was prepared from 1466 by reaction with trifluoromethanesulfonic anhydride (Tf20) in the presence of ethyldiisopropylamine. The palladium(O)-catalyzed cross-coupling of the triflate 1467 with the 3-(tributylstannyl)indole 1468 afforded the vinylindole 1469 in 89% yield. Deprotection of both nitrogen atoms with sodium ethoxide in ethanol to 1470, followed by photocyclization in the presence of iodine as the oxidizing agent provided the indolocarbazole 1471. Finally, reductive cyclization of 1471 with sodium borohydride-cobaltous chloride led to staurosporinone (293) in 40% yield (790) (Scheme 5.248). 

Carboxy-2-pyridylthio)propionic acids, prepared by the reaction of 2-mercatopyridin-3-carboxylic acid with 3-bromopropionic acid in aqueous KOH, undergo cyclization upon treatment with anhydrous sodium acetate and acetic anhydride to afford 2,3-dihydrothiopyrano[2,3-3]pyridin-4(4//)-ones. These products undergo further reaction with phenylhydrazine to give the phenylhydrazone (isolated) and then Fischer indole cyclization to give novel 5/7,1177-pyrido[2, 3 2,3]thiopyrano[4,3-3]indoles <2000JHC379>. 

Bacteria Proteins, peptides, propionic acid, indole, PAFA Antimicrobial Boobathy et al. (2009) Taylor et al. (2007) Devi et al. (2010) Patnayak and Sree (2005)... 

Indole-3-propionic acid [830-96-6] M 189.2, m 134-135°. Recrystd from EtOH/water [James and Ware JPC 89 5450 7955]. 

The reaction of nitroarenes with silyl end ethers and ketene silyl acetals in MeCNATiF with 1 equiv. of TASF, followed by in situ oxidation with Br2 or DDQ, provides an easy route to a-nitroaryl carbonyl compounds (Scheme l).12 The use of these compounds as reagents for the synthesis of arylacetic acids, propionic acids, indoles, 2-indolinones and other heterocyclic compounds has recently been described.88... 

In addition to tryptophan, /3-methylindole, indole-3-acetic acid and indole-3-propionic acid were tested under identical conditions and molar concentrations. The intensities of the color developed with 30 percent perchloric acid alone were in the order tryptophan < indole-3-acetic acid < indole-3-propionic acid < /3-methylindole. The first three of these indole derivatives produced red condensates with desoxyribose in perchloric acid, that due to indole-3-acetic acid being markedly less than that arising from the other two. 

Competitive inhibition of the carboxypeptidase from A. saitoi by small substrates was found with hydrocinnamic acid, indole-3-propionic acid, and 4-phenylbutyric acid [80], The K for hydrocinnamic acid inhibition was 4 x 10 4 M. Diisopropylfluorophosphate (DFP) and tosyl-L-phenylalanylchloromethane (TPCK) were also powerful inhibitors of the carboxypeptidase from A. oryzae (80). />-Chloromercuribenzoate (PCMB) and iodoacetic acid were also powerful inhibitors of the carboxypeptidase from A. saitoi, while the inhibitors of DFP, TPCK, PCMB, and iodoacetic acid on the carboxypeptidase from A. saitoi were less than that of A. oryzae [80], As the carboxypeptidase activity of A. saitoi has no effect when used with ethylenediaminetetraacetate (EDTA) and o-phenanthroline, the enzyme is a different type of carboxypeptidase from those of the pancreatic sources, carboxypeptidase A and carboxypeptidase B [80],... 

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