4688-60-2Relevant articles and documents
Enantioselective synthesis and stereochemical determination of the highly reduced polyketide ishigamide
Du, Danyao,Ishigami, Ken,Katsuta, Ryo,Katsuyama, Yohei,Nukada, Tomoo,Ohnishi, Yasuo,Seo, Mitsuki,Yajima, Arata
, p. 148 - 153 (2022/03/18)
Ishigamide was isolated as a metabolite of a recombinant strain of Streptomyces sp. MSC090213JE08 and its unsaturated fatty acid moiety has been confirmed in vitro to be synthesized by a type II PKS. Biosynthesis of such a highly reduced polyketide by a type II PKS is worthy of note. However, absolute configuration of ishigamide remained unknown. (R)-Ishigamide was synthesized enantioselectively employing Stille coupling and Wittig reaction between three units, vinyl iodide, stannyldienal, and Wittig salt. Stereochemistry of natural ishigamide was determined to be R by chiral HPLC analysis comparing with the synthesized standard.
Simple and convenient method for the synthesis of 2-substituted glutaconaldehyde salts and 2-substituted glutaconaldehyde derivatives
Nguyen, Tuan Minh,Peixoto, Sabrina,Ouairy, Cecile,Nguyen, Tung Dinh,Benechie, Michel,Marazano, Christian,Michel, Patrick
experimental part, p. 103 - 109 (2010/04/26)
Convenient and scalable syntheses of 2-substituted glutaconaldehyde salts were accomplished from the corresponding pyridinium salts. Glutaconaldehyde salts were additionally converted into aminopentadienal derivatives.
Synthesis of isotopically labelled L-phenylalanine and L-tyrosine
Raap, Jan,Nieuwenhuis, Saskia,Creemers, Alain,Hexspoor, Sander,Kragl, Udo,Lugtenburg, Johan
, p. 2609 - 2621 (2007/10/03)
A synthetic route to stable-isotope-substituted L-phenylalanine is presented, which allows the introduction of 13C, 15N, and deuterium labels at any position or combination of positions. For labelling of the aromatic ring, a synthetic route to ethyl benzoate (or benzonitrile) has been developed, based on the electrocyclic ring-closure of a 1,6-disubstituted hexatriene system, with in situ aromatization by elimination of one (amino) substituent. Several important (highly isotopically enriched) synthons have been prepared, namely benzonitrile, benzaldehyde, ethyl benzoate, and ethyl diphenyloxyacetate. Labelled L-phenylalanines have been synthesized from both aromatic precursors by initial conversion into sodium phenylpyruvate and subsequent transformation of this intermediate into the L-α-amino acid by an enzymatic reductive amination reaction. In this manner, highly enriched phenylalanines are obtained on the 10-gram scale and with high enantiomeric purities (≥ 99% ee). The method has been validated by the synthesis of [1'13C]-L-Phe and [2-D]-L-Phe. In addition, two methods are described for the introduction of isotopes into L-tyrosine starting from the isotopically enriched precursors benzonitrile and ethyl benzoate.