66178-04-9Relevant academic research and scientific papers
Synthesis and structure reassignment of malylglutamate, a recently discovered earthworm metabolite
Griffith, Corey M.,Feceu, Abigail,Larive, Cynthia K.,Martin, David B. C.
, p. 417 - 421 (2019/02/19)
Malylglutamate, a newly identified metabolite in earthworms, was synthesized using a traditional peptide coupling approach for assembling the amide from protected malate and glutamate precursors. The proposed structure (1) and a diastereomer were synthesized, but their NMR spectra did not match the natural sample. Further analysis of the natural sample using HMBC spectroscopy suggested an alternative attachment of the malyl moiety, and β-malylglutamate (2) diastereomers were synthesized, L,L-2 and D,D-2. NMR spectra were an excellent match with the natural sample, and chiral-phase chromatography was employed to identify (a)-β-l-malyl-l-glutamate (2) as the isomer native to Eisenia fetida.
TRIAZOLE-ISOXAZOLE COMPOUND AND MEDICAL USE THEREOF
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Paragraph 3409, (2016/06/06)
A compound represented by Formula [I]: or pharmaceutically acceptable salt thereof, wherein each symbol is as defined in the description.
α-Carboxy-β-lactones from photoinduced ring contraction of 3-diazodihydrofuran-2,4-diones
Beneke, Julia,Schobert, Rainer
supporting information, p. 773 - 776 (2013/04/10)
β-Lactones were prepared by irradiation of 3-diazodihydrofuran-2,4- diones via Wolff rearrangement proceeding with retention of the configuration of the migrating carbon atom. In the presence of alcohols or thiols, but not amines, the corresponding 3-(alkoxycarbonyl)- or 3-[(alkylsulfanyl)carbonyl]- β-lactones were obtained. 5-Alkyl-3-diazodihydrofuran-2,4-diones gave exclusively trans-3,4-disubstituted β-lactones. Georg Thieme Verlag Stuttgart · New York.
An efficient synthesis of carlosic acid and other 5-carboxymethyltetronates from malates
Schobert, Rainer,Jagusch, Carsten
, p. 2421 - 2425 (2007/10/03)
S-Carlosic acid was prepared in six steps and 32% yield from malic acid. Ring closure was effected by a domino addition-Wittig alkenation reaction with Ph3PCCO. A variant employing resin-bound malates furnished immobilized 5-carboxymethyltetron
Design and synthesis of sulfur based inhibitors of matrix metalloproteinase-1.
Fujisawa, Tetsunori,Odake, Shinjiro,Ogawa, Yuji,Yasuda, Junko,Morita, Yasuo,Morikawa, Tadanori
, p. 239 - 252 (2007/10/03)
Fibroblast collagenase (MMP-1), a member of the matrix metalloproteinases family, is believed to be a pathogenesis of arthritis, by cleaving triple-helical type II collagen in cartilage. From the similarity of the active site zinc binding mode with hydroxamate, we designed and synthesized alpha-mercaptocarbonyl possessing compounds (3-5), which incorporated various peptide sequences as enzyme recognition sites. The P4-P1 peptide incorporating compound (3) exhibited as potent inhibition as the hydroxamate (1) and the carboxylate (2) type inhibitors, with an IC50 of 10(-6) M order against MMP-1. But the inhibitor (3) related compounds (6-8) displayed decreased or no inhibitory potencies. These results suggest that the existence of both the carbonyl and thiol groups might be critical for the inhibition, and the distance between the two functional groups is important for inhibitory potency. For Pn' peptide incorporating compounds (4a-k), except for 4h and 4k, all compounds showed IC50 values under sub-nanomolar. Among them, for potent inhibition, Leu was better than Phe and Val as the P1' amino acid, and the P2' position amino acid was necessary, and preferentially Phe. Insertion of the Pn peptide into 4d or 4k, giving compounds 5a-c, did not increase the activities of 4d and 4k. Substitution of the mercapto group with other functional groups lost the activity of compound 4a. The stereochemical preference at the thiol-attached position was also determined by preparation of both isomers of 4a. It was found that the S configuration compound (36b) is approximately 100 times more potent than the corresponding R-isomer (36a).
Synthesis and biological evaluation of analogues of the antibiotic pantocin B
Sutton,Clardy
, p. 9935 - 9946 (2007/10/03)
Strains of the bacteria Erwinia herbicola produce antibiotics that effectively control E. amylovora, the bacterial pathogen responsible for the plant disease fire blight. Pantocin B was the first of these antibiotics to be characterized, and a flexible sy
Preparation of free and of specifically protected oligo[β-malic acids] for enzymatic degradation studies
Krell, Christoph M.,Seebach, Dieter
, p. 1207 - 1218 (2007/10/03)
The polyanionic poly[β-(S)-malic acids] (β-PMA) occur in slime molds (myxomycetes), black yeasts and other fungi and are involved in DNA replication. In order to be able to study the cleavage mechanism of β-PMA hydrolases, we have synthesized cyclic and linear oligomers of malic acid (β-OMA) consisting of up to eight residues. To this end, fragments with three different protecting groups were prepared, with allyl ester groups on the C-terminus, TBDPS groups at the O-terminus, and benzyl ester groups at the side chains (Schemes 2, 3, 7). Selective deprotection and fragment coupling (COCl2/C5H5N/CH2Cl2/-75 °C) gave dimers, tetramers, and octamers, either fully protected or specifically protected at the O- or C- terminus or at the side chain acid groups, and also fully deprotected oligoacids (Schemes 3-7). The new compounds were fully characterized (R(f), IR, 1H- and 13C-NMR spectroscopy, mass spectrometry and elemental analysis or high-resolution electrospray mass spectrometry). Enzymatic degradation experiments with the previously prepared cyclo-tetramer, the unprotected, and the O- or C-terminally protected samples of linear β-OMAs show that the enzyme from Physarum polycephalum is an exo-hydrolase cleaving the chain from the O-terminus.
The total synthesis of pantocin B.
Sutton,Clardy
, p. 319 - 321 (2007/10/03)
[reaction: see text] Pantocin B, an unusual antibiotic produced by Erwinia herbicola, effectively controls E. amylovora, the pathogen causing the plant disease fire blight. A total synthesis of pantocin B from L-alanine, glycine, and L-malic acid is repor
