91523-50-1 | Page 3 of 3 | Heterocyclic Building Blocks-Naphthyridine

What I Wish Everyone Knew About 91523-50-1

There is still a lot of research devoted to this compound(SMILES：OC(=O)C1NCCC2=C1C=CC(O)=C2)Related Products of 91523-50-1, and with the development of science, more effects of this compound(91523-50-1) can be discovered.

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid(SMILESS: OC(=O)C1NCCC2=C1C=CC(O)=C2,cas:91523-50-1) is researched.Formula: C5H3IO2. The article 《A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion》 in relation to this compound, is published in Green Chemistry. Let’s take a look at the latest research on this compound (cas:91523-50-1).

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids are important chiral building blocks in the pharmaceutical and fine chem. industries. However, the existing chemo-enzymic deracemization method employing D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) suffers from the requirement for a large excess of a nonselective chem. reducing agent. To explore an alternative method, we envisaged a concurrent biocatalytic oxidation and reduction cascade in one pot. Herein, we report a novel biocatalytic route for the asym. reduction of 3,4-dihydroisoquinoline-1-carboxylic acids employing Δ1-piperidine-2-carboxylate/Δ1-pyrrolidine-2-carboxylate reductase from Pseudomonas putida KT2440 (PpDpkA) as a biocatalyst, yielding the corresponding (S)-1-carboxyl-substituted tetrahydroisoquinolines with high conversions and enantiomeric excess (>99% ee). By combining FsDAAO and PpDpkA in one pot, a fully biocatalytic method was demonstrated for the deracemization of a range of racemic 1-carboxyl substituted tetrahydroisoquinolines to produce the corresponding (S)-enantiomers with >99% conversions and >99% ee. Furthermore, preparative-scale biotransformation of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid gave the (S)-enantiomer with 89% isolated yield and >99% ee. Taken together, we provide an enantioselective biocatalytic redox cascade method for the one-pot synthesis of enantiopure 1,2,3,4-tetrahydroisoquinoline carboxylic acids.

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Fun Route: New Discovery of 91523-50-1

If you want to learn more about this compound(6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid)Synthetic Route of C10H11NO3, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(91523-50-1).

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Chemoenzymatic Approach to (S)-1,2,3,4-Tetrahydroisoquinoline Carboxylic Acids Employing D-Amino Acid Oxidase, published in 2019, which mentions a compound: 91523-50-1, Name is 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, Molecular C10H11NO3, Synthetic Route of C10H11NO3.

Optically pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids constitute an important class of building blocks for the synthesis of natural products and synthetic pharmaceuticals. However, redox deracemization of racemic 1,2,3,4-tetrahydroisoquinoline carboxylic acids as an attractive method is still challenging for the lack of suitable oxidoreductases. Herein, a D-amino acid oxidase from Fusarium solani M-0718 (FsDAAO) with broad substrate scope and excellent enantioselectivity was exploited through genome mining, and applied for the kinetic resolution of a number of racemic 1- and 3-carboxyl substituted tetrahydroisoquinolines to yield the corresponding (S)-enantiomers with excellent enantiomeric excess (ee) values (up to >99%). By using FsDAAO in combination with ammonia-borane in one pot, deracemization of these racemic carboxyl-substituted tetrahydroisoquinolines was achieved with conversions up to >98% and >99% ee. Preparative-scale deracemization of racemic 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid was also demonstrated with good isolated yields (82% and 73%, resp.) and ee>99%. Our study provides an effective method for the synthesis of enantiomeric pure 1,2,3,4-tetrahydroisoquinoline carboxylic acids. This method is expected to provide access to chiral carboxyl-substituted 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-ss-carbolines.

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Some scientific research about 91523-50-1

If you want to learn more about this compound(6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid)Related Products of 91523-50-1, you may wish to communicate with the author of the article,or consult the relevant literature related to this compound(91523-50-1).

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Green Chemistry called A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion, Author is Ju, Shuyun; Qian, Mingxin; Li, Jing; Xu, Gang; Yang, Lirong; Wu, Jianping, which mentions a compound: 91523-50-1, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3, Related Products of 91523-50-1.

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Derivation of elementary reaction about 91523-50-1

Here is a brief introduction to this compound(91523-50-1)Quality Control of 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, if you want to know about other compounds related to this compound(91523-50-1), you can read my other articles.

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called A biocatalytic redox cascade approach for one-pot deracemization of carboxyl-substituted tetrahydroisoquinolines by stereoinversion, published in 2019, which mentions a compound: 91523-50-1, Name is 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid, Molecular C10H11NO3, Quality Control of 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid.

Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem

Analyzing the synthesis route of 91523-50-1

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 91523-50-1, is researched, SMILESS is OC(=O)C1NCCC2=C1C=CC(O)=C2, Molecular C10H11NO3Journal, Article, Bioorganic & Medicinal Chemistry called Exploiting differences in caspase-2 and -3 S2 subsites for selectivity: Structure-based design, solid-phase synthesis and in vitro activity of novel substrate-based caspase-2 inhibitors, Author is Maillard, Michel C.; Brookfield, Frederick A.; Courtney, Stephen M.; Eustache, Florence M.; Gemkow, Mark J.; Handel, Rebecca K.; Johnson, Laura C.; Johnson, Peter D.; Kerry, Mark A.; Krieger, Florian; Meniconi, Mirco; Munoz-Sanjuan, Ignacio; Palfrey, Jordan J.; Park, Hyunsun; Schaertl, Sabine; Taylor, Malcolm G.; Weddell, Derek; Dominguez, Celia, the main research direction is proline peptide preparation caspase inhibitor Huntington disease.SDS of cas: 91523-50-1.

Several caspases have been implicated in the pathogenesis of Huntington’s disease (HD); however, existing caspase inhibitors lack the selectivity required to investigate the specific involvement of individual caspases in the neuronal cell death associated with HD. In order to explore the potential role played by caspase-2, the potent but non-selective canonical Ac-VDVAD-CHO caspase-2 inhibitor 1 was rationally modified at the P2 residue in an attempt to decrease its activity against caspase-3. With the aid of structural information on the caspase-2, and -3 active sites and mol. modeling, a 3-(S)-substituted-L-proline along with four addnl. scaffold variants were selected as P2 elements for their predicted ability to clash sterically with a residue of the caspase-3 S2 pocket. These elements were then incorporated by solid-phase synthesis into pentapeptide aldehydes 33a-v. Proline-based compound 33h bearing a bulky 3-(S)-substituent displayed advantageous characteristics in biochem. and cellular assays with 20- to 60-fold increased selectivity for caspase-2 and ∼200-fold decreased caspase-3 potency compared to the reference inhibitor 1. Further optimization of this prototype compound may lead to the discovery of valuable pharmacol. tools for the study of caspase-2 mediated cell death, particularly as it relates to HD.

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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem