Optical Resolution of (RS)-Mercaptosuccinic Acid and Syntheses of Four Stereoisomers of 2-Amino-3-1(1,2-dicarboxyethyl)sulfanyl)propanoic Acid.

Shiraiwa, Tadashi; Ohkubo, Masanori; Kubo, Motoki; Miyazaki, Hisao; Takehata, Masaki; Izawa, Hisashi; Nakagawa, Kazuo; Kurokawa, Hidemoto

doi:10.1248/cpb.46.1364

Cited by 8 publications

(7 citation statements)

References 1 publication

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“…The asymmetric unit of (I) contains an [(S)-Hpea] + cation and an [(R)-H 2 msa] À anion. The absolute configurations of cation and anion, which were confirmed by the Flack (1983) parameter, are consistent with the previous prediction made by optical rotation measurements (Shiraiwa et al, 1998). In (I), the amine group of pea is protonated to form a [Hpea] + cation, while one of the two carboxy groups of thiomalic acid (C3, O1 and O2) is protonated and the other (C4, O3 and O4) is deprotonated to form a [H 2 msa] À anion (Fig.…”

Section: Commentsupporting

confidence: 91%

“…Compound (I) was prepared according to the method of Shiraiwa et al (1998). (RS)-H 3 msa (5.0 g, 33 mmol) and (S)-pea (4.0 g, 33 mmol) were dissolved in propan-1-ol (27 ml).…”

Section: Methodsmentioning

confidence: 99%

“…{Na 2 [Au(msa)]Á-1.75H 2 O} n , by Nomiya et al (1995). For example, LeBlanc et al (1997) reported the asymmetric synthesis of pure (R)thiomalic acid from l-aspartic acid in three steps, while Shiraiwa et al (1998) reported the optical resolution of the racemic H 3 msa with the use of (S)-pea (pea = 1-phenylethanamine), which led to the preferential crystallization of the title compound, [(S)-Hpea] + Á[(R)-H 2 msa] À , (I). The latter method is undoubtedly superior to the former, but the resulting salt, (I), has not been crystallographically characterized.…”

Section: Commentmentioning

confidence: 99%

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An optically resolved crystal of thiomalate: (S)-1-phenylethanaminium (R)-thiomalate

2012

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The asymmetric unit of the optically resolved title salt, C(8)H(12)N(+)·C(4)H(5)O(4)S(-), contains a 1-phenylethanaminium monocation and a thiomalate (3-carboxy-2-sulfanylpropanoate) monoanion. The absolute configurations of the cation and the anion are determined to be S and R, respectively. In the crystal, cation-anion N-H···O hydrogen bonds, together with anion-anion O-H···O and S-H···O hydrogen bonds, construct a two-dimensional supramolecular sheet parallel to the ab plane. The two-dimensional sheet is linked with the upper and lower sheets through C-H···π interactions to stack along the c axis.

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Section: Commentsupporting

confidence: 91%

“…Compound (I) was prepared according to the method of Shiraiwa et al (1998). (RS)-H 3 msa (5.0 g, 33 mmol) and (S)-pea (4.0 g, 33 mmol) were dissolved in propan-1-ol (27 ml).…”

Section: Methodsmentioning

confidence: 99%

Section: Commentmentioning

confidence: 99%

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An optically resolved crystal of thiomalate: (S)-1-phenylethanaminium (R)-thiomalate

2012

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“…Resolution of Racemic MSA. A modified version of the method published by Shiraiwa et al 26 was used to resolve racemic MSA using (1S,2S)-2-amino-1-phenyl-1,3-propanediol (APP). A 2:1 resolving reagent:MSA molar ratio was mixed in 10−11 mL of methanol (HPLC grade, BDH Chemicals) and stirred for 2−3 h. The precipitate (R)-MSA•(S)-APP was filtered, collected, and washed with 6−8 mL of methanol.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Substrate Specificity in Thiol Dioxygenases

et al. 2019

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Thiol dioxygenases make up a class of ferrous iron-dependent enzymes that oxidize thiols to their corresponding sulfinates. X-ray diffraction structures of cysteine-bound cysteine dioxygenase show how cysteine is coordinated via its thiolate and amine to the iron and oriented correctly for O atom transfer. There are currently no structures with 3-mercaptopropionic acid or mercaptosuccinic acid bound to their respective enzymes, 3-mercaptopropionate dioxygenase or mercaptosuccinate dioxygenase. Sequence alignments and comparisons of known structures have led us to postulate key structural features that define substrate specificity. Here, we compare the rates and reactivities of variants of Rattus norvegicus cysteine dioxygenase and 3-mercaptopropionate dioxygenases from Pseudomonas aureginosa and Ralstonia eutropha (JMP134) and show how binary variants of three structural features correlate with substrate specificity and reactivity. They are (1) the presence or absence of a cis-peptide bond between residues Ser158 and Pro159, (2) an Arg or Gln at position 60, and (3) a Cys or Arg at position 164 (all RnCDO numbering). Different permutations of these features allow sulfination of l-cysteine, 3-mercaptopropionic acid, and (R)-mercaptosuccinic acid to be promoted or impeded.

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“…As a result, we turned back to use steroid 6 to react with different nucleophiles possessing hydrophilic properties at the C‐21 position for further derivation (see Table ). At first, we gifted amino acids including D‐Ornithine hydrochloride and L‐cysteine towards C‐21 bromosteroid 6 in presence of hindered amine including N , N ‐diisopropylethylamine or triethylamine in DMF or EtOH to obtain the corresponding C‐21 amino acid‐steroid adducts 11 and 12 in 72% and 24% yields, respectively (see Table ). Based on the experimental results, we found the lower yield was observed in L‐cysteine as a nucleophile because of the poor solubility in EtOH solution.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and antiproliferative activity of 3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-one with a C-21 hydrophilic substituent

et al. 2017

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A series of 3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-ones 7-15 possessing C-21 hydrophilic substituents were synthesized from the corresponding C21-bromo steroid 6 in 24%-89% yields. The hydrophilic groups include amino group from Delépine reaction, hydroxyl group from the hydrolysis by cesium formate in anhydrous MeOH, and amino acids, hydrazinecarboxamide, piperazine, and imidazolyl from nucleophilic substitution. Acylation and O-glycosylation of the resulting C-21 hydroxylsteroid also afforded the corresponding acylated and glycosylated products in excellent yield (77%-89%). Among the compounds, aminosteroid 7 and piperazinyl steroid 14 were most potent against the proliferation of human prostate cancer PC-3 cells with IC 50 values of 42 and 82 μmol L −1 , respectively.

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Optical Resolution of (RS)-Mercaptosuccinic Acid and Syntheses of Four Stereoisomers of 2-Amino-3-1(1,2-dicarboxyethyl)sulfanyl)propanoic Acid.

Cited by 8 publications

References 1 publication

An optically resolved crystal of thiomalate: (S)-1-phenylethanaminium (R)-thiomalate

An optically resolved crystal of thiomalate: (S)-1-phenylethanaminium (R)-thiomalate

Substrate Specificity in Thiol Dioxygenases

Synthesis and antiproliferative activity of 3α-hydroxyl-3β-methoxymethyl-5α-pregnan-20-one with a C-21 hydrophilic substituent

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