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Gas up: A cyclometalated iridium complex is found to catalyze the dehydrogenation of various benzofused N-heterocycles, thus releasing H 2. Driven by as low as 0.1 mol % catalyst, the reaction affords quinolines, indoles, quinoxalines, isoquinolines, and beta-carbolines in high yields. Copyright

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Isoquinoline – Wikipedia,
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A catalytic oxidation system, a CuCl2-O2 system, was efficient for dehydrogenation of 1,2,3,4-tetrahydroisoquinolines to 3,4-dihydroquinolines.Oxidation of 1,2,3,4-tetrahydroquinoline was also carried out.

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Isoquinoline – Wikipedia,
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In mammals, the role of a prolactin-releasing factor (PRF) in the acute changes of prolactin (PRL) secretion that usually occur after challenges (e.g., suckling stimulus or stress) of homeostasis has been suspected for a long time. We have recently observed that 1-methyl-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinoline, salsolinol (SAL), produced by the hypothalamus and the neuro-intermediate lobe (NIL) of the pituitary gland, can selectively release PRL from the anterior lobe (AL). Moreover, binding sites for SAL have been detected in areas like median eminence, NIL, and AL. It has been proposed that SAL is a putative endogenous PRF. We have also found that a structural analogue of SAL, 1-methyl-3,4-dihydroisoquinoline (1MeDIQ), is able to block dose-dependently SAL-,suckling-,and immobilization (IMO) stress-induced release of PRL without having any influence on alpha-methyl-p-tyrosine (alphaMpT)-induced PRL responses. Neither SAL nor 1MeDIQ has any effect on alpha-melanocyte-stimulating hormone (alphaMSH), adrenocorticotrophic hormone (ACTH), beta-endorphin (beta-END) and arginine-vasopressin (AVP) secretion. Moreover, SAL-induced PRL response was attenuated in male rats pretreated with dexamethasone (DEX). These results strongly suggest that SAL has an important role in the regulation of PRL release induced by physiologic and environmental stimuli; therefore, it can be considered as the strongest candidate for being the PRF in the hypothalamo-hypophysial system. Our findings also indicate that the adrenal steroids may play an inhibitory feedback role in SAL-mediated PRL response.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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Simple tripeptides are shown here to be versatile ligands for iridium-catalyzed transfer hydrogenations affording large acceleration effects. A water-soluble iridium complex with Gly-Gly-Phe, for example, catalyzes the reduction of diverse ketones, aldehydes, and imines by formate with turnover frequencies rivaling or outperforming those of established ligand systems. Regioselective reduction of coenzyme NAD+ to NADH illustrates the potential utility of this system for biotechnological applications. Because peptides are genetically encodable, they represent an attractive class of foldamer ligands for creating artificial metalloenzymes.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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A highly convergent, regioselective synthesis of apomorphine analogues is described. It relies on the intermolecular cycloaddition between a 1-methylene-1,2,3,4-tetrahydroisoquinoline and an asymmetrically substituted aryne.

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Artificial metalloenzymes enable the engineering of the reaction microenvironment of the active metal catalyst by modification of the surrounding host protein. We report herein the optimization of an artificial imine reductase (ATHase) based on biotin-streptavidin technology. By introduction of lipophilic amino acid residues around the active site, an 8-fold increase in catalytic efficiency compared with the wild type imine reductase was achieved. Whereas substrate inhibition was encountered for the free cofactor and wild type ATHase, two engineered systems exhibited classical Michaelis-Menten kinetics, even at substrate concentrations of 150 mM with measured rates up to 20 min -1.

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Isoquinoline – Wikipedia,
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Imines and carboxylic acids have been directly coupled using propylphosphonic acid anhydride and NEt(i-Pr)2 to give N-acyliminium ions, which were intramolecularly trapped with oxygen, nitrogen, sulfur, and carbon nucleophiles to provide a wide range of structurally diverse heterocycles.

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Isoquinoline – Wikipedia,
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Imine reductases (IRED) are promising catalysts for the synthesis of optically pure secondary cyclic amines. Three novel IREDs from Paenibacillus elgii B69, Streptomyces ipomoeae 91-03 and Pseudomonas putida KT2440 were identified by amino acid or structural similarity search, cloned and recombinantly expressed in E. coli and their substrate scope was investigated. Besides the acceptance of cyclic amines, also acyclic amines could be identified as substrates for all IREDs. For the IRED from P. putida, a crystal structure (PDB-code 3L6D) is available in the database, but the function of the protein was not investigated so far. This enzyme showed the highest apparent E-value of approximately Eapp = 52 for (R)-methylpyrrolidine of the IREDs investigated in this study. Thus, an excellent enantiomeric purity of >99% and 97% conversion was reached in a biocatalytic reaction using resting cells after 24 h. Interestingly, a histidine residue could be confirmed as a catalytic residue by mutagenesis, but the residue is placed one turn aside compared to the formally known position of the catalytic Asp187 of Streptomyces kanamyceticus IRED.

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Isoquinoline – Wikipedia,
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In this paper novel spiro-tetra- (5,5′), spiro-hexa- (6), and spiro-octahydroindolizines (7) are presented.The synthesis of 5, 5′, 6a, b, and 7 is described.LIS are employed for structure elucidation.UV kinetics – especially flash spectroscopy – demonstrate that a reversible electrocyclic reaction of the tetrahydroindolizines 5 is responsible for the photochromic properties of 5. 5’h is an exception, whereas 6a, b, and 7 are not photochromic at all.

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Isoquinoline – Wikipedia,
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The design of a recombinant whole-cell catalyst and its utilization in the asymmetric reduction of 1-methyl-3,4-dihydroisoquinoline chosen as a model substrate for cyclic imines is presented. As ?designer cells? E. coli cells bearing the two enzymes imine reductase and glucose dehydrogenase (for in situ-cofactor recycling) were constructed, which turned out to be suitable for the asymmetric reduction of 1-methyl-3,4-dihydroisoquinoline at low biocatalyst loading of 2 g/L up to 10 g/L of lyophilized cells, leading to both high conversion and enantioselectivity of >99% ee of the resulting amine. The stoichiometric reducing agent is readily available D-glucose, and a proof of concept for running the reactions at elevated substrate concentration of up to 100 mM was demonstrated.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H865N – PubChem