Simple peptides. II. Syntheses and properties of taurine-dipeptides containing neutral .ALPHA.-amino acid.

Ienaga, Kazuharu; Higashiura, Kunihiko; Toyomaki, Yoshio; Matsuura, Hirohide; Kimura, Hiroshi

doi:10.1248/cpb.36.70

Cited by 9 publications

(20 citation statements)

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“…Compound 1-I was synthesized by coupling 3-indoleglyoxylic acid ( 6 ) with taurine ( Scheme 1 ) in the presence of N -(3-dimethylaminopropyl)- N′ -ethylcarbodiimide (EDCI), N -hydroxybenzotriazole (HOBt) and dimethylformamide (DMF) at room temperature (rt) for 21 h (64% yield) [ 26 ]. Both 1 H and 13 C NMR data of the synthetic 1-I completely matched those of the natural product 1 ( Table 3 ) confirming that 1-I was the structure of 1 .…”

Section: Resultsmentioning

confidence: 99%

Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

et al. 2015

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Cnemidocarpa stolonifera is an underexplored marine tunicate that only occurs on the tropical to subtropical East Coast of Australia, with only two pyridoacridine compounds reported previously. Qualitative analysis of the lead-like enhanced fractions of C. stolonifera by LC-MS dual electrospray ionization coupled with PDA and ELSD detectors led to the identification of three new natural products, stolonines A–C (1–3), belonging to the taurine amide structure class. Structures of the new compounds were determined by NMR and MS analyses and later verified by total synthesis. This is the first time that the conjugates of taurine with 3-indoleglyoxylic acid, quinoline-2-carboxylic acid and β-carboline-3-carboxylic acid present in stolonines A–C (1–3), respectively, have been reported. An immunofluorescence assay on PC3 cells indicated that compounds 1 and 3 increased cell size, induced mitochondrial texture elongation, and caused apoptosis in PC3 cells.

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Section: Resultsmentioning

confidence: 99%

Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

et al. 2015

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“…Compound 16a was obtained as a white solid (0.95 g, 91%) according to the general procedure, starting from DCC (1.29 g, 6.27 mmol), Boc-Gly-OH 15a (1.0 g, 5.70 mmol), N-hydroxy succinimide (0.68 g, 5.93 mmol) in THF (20 mL) and taurine sodium salt (0.84 g, 5.70 mmol) in dioxane-water (1:1, 30 mL). 1 H NMR (300 MHz, D2O) δ = 3.82 (s, 2H, CH2-Gly), 3.67 (t, J = 6.0 Hz, 2H, CH2αCH2SO3H), 3.13 (t, J = 6.8 Hz, 2H, CH2CH2βSO3H); 13 C NMR (75 MHz, D2O) δ = 166.5 (CO-Gly), 49.1 (CH2CβH2SO3H), 40.1 (CH2-Gly), 34.8 (CαH2CH2SO3H); HRMS for C4H10N2O4S [M-H]calcd. : 181.0288, found: 181.0290.…”

Section: Thymidine-5'-taurine Phosphoramidate Ammonium Salt (1)mentioning

confidence: 99%

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Groaz

Margamuljana

et al. 2015

Org. Biomol. Chem.

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Novel unnatural 5'-phosphoramidate nucleosides, capable of being processed as substrates by DNA polymerases for multiple nucleotide incorporations, have been designed. The mimics feature metabolites such as taurine and a broad range of aliphatic sulfonates coupled through a P-N bond to the 5'-phosphate position of deoxynucleotides, to allow binding interactions in the enzyme active site. The utility of all of the analogues as pyrophosphate mimics was demonstrated for the chain elongation of DNA, using both thermophilic and mesophilic microbial polymerases.

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“…From 9 (0.05 g, 0.08 mmol); preparative HPLC: 90% H 2 O (0.1% TFA) and 10% MeOH to 100% MeOH in 10 min, 100% MeOH for 2 min; yield: 40 mg (84%, 0.13 mmol); brown solid; mp >250 °C (Lit. 15…”

Section: Hydrochloride Of (S)-n-phenylalanyltaurine (23)mentioning

confidence: 99%

“…6a Only few examples showed that taurine and its sodium salt can be acylated by acetic and butyric anhydride, lactones, 13 chloroformates, 14 or amino acids with N,N′-dicyclohexylcarbodiimide/N-hydroxy-5-norbornene-2,3-dicarboxylimide. 15 To overcome the aforementioned difficulties, we chose a synthetic entry to a series of N-acylated taurine derivatives without applying taurine itself as acyl acceptor. Instead, the corresponding disulfides were prepared and investigated as substrates of an oxidative conversion into the aliphatic and aromatic sulfonic acids (Table 1).…”

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confidence: 99%

Oxidation of Disulfides to Taurine and Sulfanilic Acid Derivatives

et al. 2015

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Taurine (2-aminoethanesulfonic acid) is a representative substructure in biologically active compounds, but can raise difficulties in direct coupling reactions. In this study, the synthesis of taurine-derived sulfonic acids and analogous aromatic sulfonic acids was accomplished by a performic acid promoted oxidation of corresponding symmetrical disulfide precursors. In some of the products, the taurine or sulfanilic acid nitrogen atom is incorporated in a heterocyclic scaffold or part of a peptide bond in dipeptide mimetics.

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Simple peptides. II. Syntheses and properties of taurine-dipeptides containing neutral .ALPHA.-amino acid.

Cited by 9 publications

References 0 publications

Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

Isolation and Total Synthesis of Stolonines A–C, Unique Taurine Amides from the Australian Marine Tunicate Cnemidocarpa stolonifera

Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

Oxidation of Disulfides to Taurine and Sulfanilic Acid Derivatives

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