10569-72-9Relevant articles and documents
A new enantioselective synthesis of β-amino acids
Saylik, Dilek,Campi, Eva M.,Donohue, Andrew C.,Jackson,Robinson, Andrea J.
, p. 657 - 667 (2001)
Enantioselective hydrogenation of some α,β-unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the α-carbon using Rh-DuPHOS catalysts afforded β-amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the α,β-unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported.
Diastereoselective total synthesis and structural confirmation of surugamide F
Kuranaga, Takefumi,Fukuba, Atsuki,Ninomiya, Akihiro,Takada, Kentaro,Matsunaga, Shigeki,Wakimoto, Toshiyuki
, p. 637 - 641 (2018)
Surugamide F is a linear decapeptide (1) isolated along with the cyclic octapeptides surugamides A–E (2–6), from a marine-derived Streptomyces species. The linear peptide 1 is produced by two nonribosomal peptide synthetases (NRPSs) encoded in adjacent open reading frames, which are further flanked by an additional pair of NRPS genes responsible for the biosyntheses of the cyclic peptides 2–6. While the cyclic peptides 2–6 were identified to be cathepsin B inhibitors, the biological activity of the new metabolite 1 still remained unclear. In order to elucidate its unique biosynthetic pathway and biological activity in detail, we planned to develop an efficient synthetic route toward 1. Here we report the diastereoselective total synthesis of 1, utilizing 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase peptide synthesis. During this study, we found that the structural correction of 1 was required, due to the mislabeling of the commercially obtained 3-amino-2-methylpropionic acid, and the true structure of 1 was corroborated by the chemical synthesis and chromatographic comparison.
Meteorites as catalysts for prebiotic chemistry
Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto
, p. 16916 - 16922 (2013)
From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.
New biocatalytic route for the production of enantioenriched β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils
Martínez-Gómez, Ana Isabel,Clemente-Jiménez, Josefa María,Rodríguez-Vico, Felipe,Kanerva, Liisa T.,Li, Xiang-Guo,Heras-Vázquez, Francisco Javier Las,Martínez-Rodríguez, Sergio
, p. 2090 - 2096 (2012)
Taking advantage of the catalytic promiscuity of pyrimidine-catabolism enzymes (dihydropyrimidinase (E.C. 3.5.2.2), N-carbamoyl-β-alanine amidohydrolase (E.C. 3.5.1.6)), the production of different β-alanine derivatives starting from 5- and 6-monosubstituted dihydrouracils has been evaluated using a mimesis approach. In this work, the S-enantioselective character of dihydropyrimidinase from Sinorizhobium meliloti toward 6-monosubstituted dihydrouracil derivatives has been shown. An inverted R-/S-enantioselectivity of N-carbamoyl-β-alanine amidohydrolase from Agrobacterium tumefaciens toward two different N-carbamoyl-β-amino acids has been proved. Our results have shown for the first time that this mimetic tandem constitutes an interesting biotechnological tool for the preparation of different β-alanine derivatives in an environmentally friendly way, allowing the production of enantioenriched (R)-α-phenyl-β-alanine (e.e. > 95%) and (R)-α-methyl-β-alanine (e.e. > 90%).
Absolute Configuration and Antibiotic Activity of Piceamycin
Beom, Ji Yoon,Byun, Woong Sub,Chung, Beomkoo,Hong, Suckchang,Jeon, Chang-Wook,Kang, Saeyeon,Kwak, Youn-Sig,Lee, Jeeyeon,Lee, Sang Kook,Oh, Dong-Chan,Oh, Ki-Bong,Shin, Jongheon,Shin, Yern-Hyerk,Yoon, Yeo Joon
, (2020)
The cultivation of a Streptomyces sp. SD53 strain isolated from the gut of the silkworm Bombyx mori produced two macrolactam natural products, piceamycin (1) and bombyxamycin C (2). The planar structures of 1 and 2 were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen Bacillus thuringiensis and various human pathogens as well as human cancer cell lines. In particular, piceamycin potently inhibited Salmonella enterica and Proteus hauseri with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.
Modular Enzymatic Cascade Synthesis of Vitamin B5 and Its Derivatives
Abidin, Mohammad Z.,Saravanan, Thangavelu,Zhang, Jielin,Tepper, Pieter G.,Strauss, Erick,Poelarends, Gerrit J.
, p. 17434 - 17438 (2018)
Access to vitamin B5 [(R)-pantothenic acid] and both diastereoisomers of α-methyl-substituted vitamin B5 [(R)- and (S)-3-((R)-2,4-dihydroxy-3,3-dimethylbutanamido)-2-methylpropanoic acid] was achieved using a modular three-step biocatalytic cascade involving 3-methylaspartate ammonia lyase (MAL), aspartate-α-decarboxylase (ADC), β-methylaspartate-α-decarboxylase (CrpG) or glutamate decarboxylase (GAD), and pantothenate synthetase (PS) enzymes. Starting from simple non-chiral dicarboxylic acids (either fumaric acid or mesaconic acid), vitamin B5 and both diastereoisomers of α-methyl-substituted vitamin B5, which are valuable precursors for promising antimicrobials against Plasmodium falciparum and multidrug-resistant Staphylococcus aureus, can be generated in good yields (up to 70 %) and excellent enantiopurity (>99 % ee). This newly developed cascade process may be tailored and used for the biocatalytic production of various vitamin B5 derivatives by modifying the pantoyl or β-alanine moiety.
Stereochemistry of the Metabolism of the DNA Base Thymine and the Drug 5-Fluorouracil
Gani, David,Hitchcock, Peter B.,Young, Douglas W.
, p. 898 - 900 (1983)
The enzyme dihydrothymine dehydrogenase reduces both the DNA base thymine and the anti-cancer drug 5-fluorouracil by overall trans addition of hydrogen, at the si-face at C-5 and the si-face at C-6.
Tripartilactam, a cyclobutane-bearing tricyclic lactam from a Streptomyces sp. in a dung beetle's brood ball
Park, Seon-Hui,Moon, Kyuho,Bang, Hea-Son,Kim, Seong-Hwan,Kim, Dong-Gyu,Oh, Ki-Bong,Shin, Jongheon,Oh, Dong-Chan
, p. 1258 - 1261 (2012)
Tripartilactam, a structurally unprecedented cyclobutane-bearing tricyclic lactam metabolite, was discovered from Streptomyces sp. isolated from a brood ball of the dung beetle, Copris tripartitus. The structure of this compound was elucidated by the combination of NMR, MS, UV, and IR spectroscopy and multistep chemical derivatization. Tripartilactam was evaluated as a Na+/K + ATPase inhibitor (IC50 = 16.6 μg/mL).
Stereoselective α-alkylation of new chiral auxiliaries: An access to enantiomerically pure α- and α,β-substituted β-amino acids
Agami, Claude,Cheramy, Sandrine,Dechoux, Luc
, p. 1838 - 1840 (1999)
New bicyclic heterocycles 5, which are potentially useful for the enantioselective synthesis of substituted β-amino acids, have been synthesized. A study on the α-alkylation of these chiral auxiliaries is presented. An optically pure β-amino acid was obtained in excellent yield from its masked chiral derivative 6a.
The Formation of Amino Acids by the Reactions of Singlet NH with Several Carboxylic Acids
Tsunashima, Shigeru,Kitamura, Takashi,Sato, Shin
, p. 2869 - 2871 (1981)
The photolysis of hydrogen azide was studied in liquid acetic acid, propionic acid, and isobutyric acid at room temperature.The formation of amino acids was confirmed by the color reactions with ninhydrin and with chromotropic acid and by the NMR spectra.From the propionic acid, α- and β-alanine were formed in the ratio of 1.5.In the case of isobutyric acid, α- and β-aminoisobutyric acids were formed in the ratio of about 5.These results are explained by the insertion reaction of NH(a1Δ) into the C-H bonds of carboxylic acids.
