Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid<i>via</i>Optical Resolution by Preferential Crystallization of (<i>RS</i>)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride

Shiraiwa, Tadashi; Tadokoro, Kohya; Tanaka, Haruyuki; Nanba, Keiichiro; Yokono, Noriyoshi; Shibazaki, Katsuyoshi; Kubo, Motoki; Kurokawa, Hidemoto

doi:10.1271/bbb.62.2382

Cited by 9 publications

(5 citation statements)

References 7 publications

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“…Step 1: (3 R )-Thiomorpholine-3-carboxylic Acid (29b). The title compound was prepared by using the procedure described by Shiraiwa and co-workers …”

Section: Methodsmentioning

confidence: 99%

“…The title compound was prepared by using the procedure described by Shiraiwa and coworkers. 29 Step 2: 3-Oxo-3a,4,6,7-tetrahydro-3H-2-oxa-5-thia-1-aza-7aazonioindenide (31b). NaNO 2 (3.14 g, 46 mmol) was added to the 1 mol/L HCl (33.7 mL) solution of (3R)-thiomorpholine-3carboxylic acid (29b) (4.96 g, 33.74 mmol) under a nitrogen atmosphere at 0 °C and stirred for 0.5 h. The solution was extracted with CHCl 3 (5 times), and the organic layer was washed with brine.…”

Section: Preparation Of (5r)(6z)-6-(67-dihydro-4h-pyrazolo[51-c]-[14]...mentioning

confidence: 99%

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Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

et al. 2006

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The design and synthesis of a series of 6-methylidene penems containing [6,5]-fused bicycles (thiophene, imidazole, or pyrazle-fused system) as novel class A, B, and C beta-lactamase inhibitors is described. These penems proved to be potent inhibitors of the TEM-1 (class A) and AmpC (class C) beta-lactamases and less so against the class B metallo-beta-lactamase CcrA. Their in vitro and in vivo activities in combination with piperacillin are discussed. On the basis of the crystallographic structures of a serine-bound reaction intermediate of 2 with SHV-1 (class A) and GC1 (class C) enzymes, compounds 14a-l were designed and synthesized. Penems are proposed to form a seven-membered 1,4 thiazepine ring in both class A and C beta-lactamases. The interaction energy calculation for the enzyme-bound intermediates favor the formation of the C7 R enantiomer over the S enantiomer of the 1,4-thiazepine in both beta-lactamases, which is consistent with those obtained from the crystal structure of 2 with SHV-1 and GC1.

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“…Step 1: (3 R )-Thiomorpholine-3-carboxylic Acid (29b). The title compound was prepared by using the procedure described by Shiraiwa and co-workers …”

Section: Methodsmentioning

confidence: 99%

Section: Preparation Of (5r)(6z)-6-(67-dihydro-4h-pyrazolo[51-c]-[14]...mentioning

confidence: 99%

Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

et al. 2006

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“…As the authentic standard, S -(6-hydroxy)- l -cysteine was synthesized according to the literature .…”

Section: Materials and Methodsmentioning

confidence: 99%

“…As the authentic standard, S-(6-hydroxy)-L-cysteine was synthesized according to the literature. 28 S-Propyl-L-cysteine and S-butyl-Lcysteine were synthesized according to the reported method. 29 The (±)-sulfoxide of each S-substituted-L-cysteine was prepared by incubation of a 200-μL reaction mixture containing 10 mM Ssubstituted-L-cysteine, 30 mM H 2 O 2 , and 100 mM HEPES-NaOH buffer (pH 7) at 28 °C for 1 h with shaking at 900 rpm.…”

Section: Cultivation Conditionsmentioning

confidence: 99%

One-Pot Synthesis of Useful S-Substituted-l-cysteine Sulfoxides Using Genetically Engineered Escherichia coli

Mizutani,

Hara,

Takeuchi

et al. 2024

J. Agric. Food Chem.

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S-Substituted-L-cysteine sulfoxides are valuable compounds that are contained in plants. Particularly, (+)-alliin and its degraded products have gained significant attention because of their human health benefits. However, (+)-alliin production has been limited to extraction from plants and chemical synthesis; both methods have drawbacks in terms of stability and safety. Here, we proposed the enzymatic cascade reaction for synthesizing (+)-alliin from readily available substrates. To achieve a one-pot (+)-alliin production, we constructed Escherichia coli coexpressing the genes encoding tryptophan synthase from Aeromonas hydrophila ssp. hydrophila NBRC 3820 and L-isoleucine hydroxylase from Bacillus thuringiensis 2e2 for the biocatalyst. Deletion of tryptophanase gene in E. coli increased the yield about 2-fold. Under optimized conditions, (+)-alliin accumulation reached 110 mM, which is the highest productivity thus far. Moreover, natural and unnatural S-substituted-L-cysteine sulfoxides were synthesized by applying various thiols to the cascade reaction. These results indicate that the developed bioprocess would enable the supply of diverse Ssubstituted-L-cysteine sulfoxides.

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“…Compound 4 was prepared according to the reported by Musser et al, 21 and 6 was prepared according to the procedure reported by Inami et al 19 Thiomorpholine-3-carboxylic acid was prepared from cysteine according to the procedure reported by Shiraiwa et al, 23 and t-butyl 4-carbamoylthiomorpholine-3-carboxylate were prepared according to the procedure reported by Cai et al 24 t-Butyl 4-carbamoyl-1,3-thiazinane-3-carboxylate (7): To a solution of 1,3-thiazinane-4-carboxamide (1.78 g, 12.2 mmol) in THF (5 mL) was added a solution of (Boc)2O (4.0 g, 1.5 eq.) in THF (10 mL) and Et3N (5 mL).…”

Section: Preparation Of Alicyclic N-nitrosaminesmentioning

confidence: 99%

Transnitrosation of Alicyclic N-Nitrosamines Containing Sulfur Atoms in Five- or Six-Membered Rings

Inami¹,

Usui²,

Mochizuki³

2023

HETEROCYCLES

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Nitric oxide (NO) is a cell transmitter produced in vivo. Alicyclic N-nitroso compounds serve as potential NO donors in vivo due to the formation of S-nitrosoglutathione by transnitrosation. In this study, N-nitroso compounds with a thioamide group and endocyclic sulfur atoms in 5-or 6-membered rings were synthesized and the transfer of nitroso group was analyzed. All compounds synthesized exhibited transnitrosation activity under acidic condtions.N-Nitroso-1,3-thiazinane-4-carbothioamide exhibited the highest transnitrosation activity.

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Synthesis of Optically Active 1,4-Thiazane-3-carboxylic AcidviaOptical Resolution by Preferential Crystallization of (RS)-2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride

Cited by 9 publications

References 7 publications

Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

Structure-Activity Relationship of 6-Methylidene Penems Bearing 6,5 Bicyclic Heterocycles as Broad-Spectrum β-Lactamase Inhibitors: Evidence for 1,4-Thiazepine Intermediates with C7 R Stereochemistry by Computational Methods

One-Pot Synthesis of Useful S-Substituted-l-cysteine Sulfoxides Using Genetically Engineered Escherichia coli

Transnitrosation of Alicyclic N-Nitrosamines Containing Sulfur Atoms in Five- or Six-Membered Rings

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