274255-87-7Relevant academic research and scientific papers
Isolation and structural elucidation of callipeltins J-M: antifungal peptides from the marine sponge Latrunculia sp.
D'Auria, Maria Valeria,Sepe, Valentina,D'Orsi, Rosa,Bellotta, Filomena,Debitus, Cécile,Zampella, Angela
, p. 131 - 140 (2007)
Continued investigation of the polar extracts of the marine sponge Latrunculia sp. has resulted in the discovery of callipeltins J-M. The new structures were determined by interpretation of their NMR and MS data. The stereochemistry of the unusual 3-methy
Glutamate transporter blockers: Enantiomerically pure (2S,3S)- and (2S,3R)-3-methyl glutamic acids
Wehbe,Rolland,Roumestant,Martinez
, p. 1123 - 1126 (2003)
A short four-step synthesis of (2S,3R)- and (2S,3S)-3-methyl glutamic acids is reported; the (2S,3R) isomer presented a significant inhibitory effect on glutamate transport.
Polytheonamides A and B, highly cytotoxic, linear polypeptides with unprecedented structural features, from the marine sponge, Theonella swinhoei
Hamada, Toshiyuki,Matsunaga, Shigeki,Yano, Gen,Fusetani, Nobuhiro
, p. 110 - 118 (2005)
Polytheonamides A and B are highly cytotoxic polypeptides with 48 amino acid residues isolated from the marine sponge, Theonella swinhoei. The structure of polytheonamide B was determined by spectral and chemical methods, especially extensive 2D NMR experiments, which resulted in the unprecedented polypeptide structure; the N-terminal glycine blocked with a 5,5-dimethyl-2-oxo-hexanoyl group, the presence of eight tert-leucine, three β-hydroxyvaline, six γ-N-methylasparagine, two γ-N-methyl-β-hydroxyasparagine, and β,β-dimethymethionine sulfoxide residues. More significantly, it has the sequence of alternating D-and L-amino acids. Polytheonamide A is an epimer of polytheonamide B differing only in the stereochemistry of the sulfoxide of the 44th residue.
Stereospecific enzymatic transformation of α-ketoglutarate to (2S,3R)-3-methyl glutamate during acidic lipopeptide biosynthesis
Mahlert, Christoph,Kopp, Florian,Thirlway, Jenny,Micklefield, Jason,Marahiel, Mohamed A.
, p. 12011 - 12018 (2007)
The acidic lipopeptides, including the calcium-dependent antibiotics (CDA), daptomycin, and A54145, are important macrocyclic peptide natural products produced by Streptomyces species. All three compounds contain a 3-methyl glutamate (3-MeGlu) as the penultimate C-terminal residue, which is important for bioactivity. Here, biochemical in vitro reconstitution of the 3-MeGlu biosynthetic pathway is presented, using exclusively enzymes from the CDA producer Streptomyces coelicolor. It is shown that the predicted 3-MeGlu methyltransferase GlmT and its homologues Dptl from the daptomycin producer Streptomyces roseosporus and Lptl from the A54145 producer Streptomyces fradiae do not methylate free glutamic acid, PCP-bound glutamate, or Glu-containing CDA in vitro. Instead, GlmT, Dptl, and Lptl are S-adenosyl methionine (SAM)-dependent α-ketoglutarate methyltransferases that catalyze the stereospecific methylation of α-ketoglutarate (αKG) leading to (3R)-3-methyl-2-oxoglutarate. Subsequent enzyme screening identified the branched chain amino acid transaminase IIvE (SCO5523) as an efficient catalyst for the transformation of (3R)-3-methyl-2-oxoglutarate into (2S,3R)-3-MeGlu. Comparison of reversed-phase HPLC retention time of dabsylated 3-MeGlu generated by the coupled enzymatic reaction with dabsylated synthetic standards confirmed complete stereocontrol during enzymatic catalysis. This stereospecific two-step conversion of αKG to (2S,3R)-3-MeGlu completes our understanding of the biosynthesis and incorporation of β-methylated amino acids into the nonribosomal lipopeptides. Finally, understanding this pathway may provide new possibilities for the production of modified peptides in engineered microbes.
Optically pure 3 - methyl glutamic acid derivatives preparation method
-
Paragraph 0098-0100, (2017/12/28)
The invention discloses a preparation method of an optically pure 3-methyl glutamic acid derivative. The optically pure 3-methyl glutamic acid derivative is obtained through asymmetric Michael addition and a hydrolysis reaction of camphor-derived tricycloiminolactone and crotonate. The preparation method of the optically pure 3-methyl glutamic acid derivative is high in stereoselectivity and yield of an obtained product, low in production cost, and high in product purity and enantiomeric excess.
Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers
Fan, Shiming,Liu, Shouxin,Zhu, Sufang,Feng, Juan,Zhang, Zhiwei,Huang, Jing
supporting information, p. 4660 - 4663 (2017/09/11)
A general and facile methodology for temperature-dependent enantiodivergent and diastereodivergent synthesis of amino acids with one or multiple chiral centers was developed. Camphor-based tricyclic iminolactones attack electrophiles from the endo face at low temperature (-78 to -40 °C) and from the exo face at high temperature (-10 to 25 °C).
METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID
-
, (2016/05/10)
Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.
METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID
-
, (2016/11/17)
Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.
Synthesis of glutamic acid and highly functionalized pyrrolidine derivatives by utilizing tunable calcium catalysts for chemoselective asymmetric 1,4-addition and [3+2] cycloaddition reactions
Hut'Ka, Martin,Tsubogo, Tetsu,Kobayashi, Shu
, p. 1561 - 1569 (2013/06/27)
A current trend in organic chemistry is the development of highly efficient, environmentally friendly and inexpensive catalysts for asymmetric transformations. Alkaline earth metals, due to their specific chemical properties and abundance in nature, provide promising and challenging catalysts in organic synthesis. This article describes the utilization of alkaline earth metals in the development of an effective catalytic system based on calcium salts in combination with Box-type ligands. We disclose asymmetric 1,4-addition and [3+2] cycloaddition reactions using simple catalytic systems consisting of calcium chloride dihydrate, chiral ligands and tetramethylguanidine. Various Box ligands were synthesized and the most effective proved to be that bearing an indane chiral backbone and a cyano group. Depending on the structure of both glycine Schiff bases and α,β-unsaturated compounds, the corresponding Michael adducts or pyrrolidine derivatives were obtained in moderate to high yields with high enantioselectivities. Modification of the catalytic system by using more Lewis acidic calcium salts such as calcium triflate and neutral Pybox-type ligands allows a tuning of the chemoselectivity and leads to suppression of the [3+2] cycloadition reactions. Various β-substituted acrylates provided 1,4-addition adducts exclusively in high yields with moderate to high diastereo- and enantioselectivities. This methodology has broadened a synthetic route to β-branched glutamic acid derivatives and established calcium salts as useful and attractive catalysts for asymmetric catalysis. Copyright
Synthesis of non-proteinogenic amino acids using Michael addition to unsaturated orthopyroglutamate derivative
Oba, Makoto,Saegusa, Tsuneki,Nishiyama, Naohiro,Nishiyama, Kozaburo
experimental part, p. 128 - 133 (2009/04/06)
Stereoselective synthesis of non-proteinogenic amino acids via Michael addition to 3,4-didehydropyroglutamate derivative in which the carboxyl function is protected as a 2,7,8-trioxabicyclo[3.2.1]octane (ABO ester) group is described. The obtained 3-subst
