1509-35-9Relevant articles and documents
A new simple preparation of D-alloisoleucine suitable for large-scale manufacture
Noda, Hirofumi,Sakai, Kenichi,Murakami, Hisamichi
, p. 2649 - 2652 (2002)
D-Alloisoleucine (D-aIle) was obtained by the resolution of the epimer mixture of L-isoleucine (L-Ile) and D-aIle, which was formed by epimerization of L-Ile, with a resolving agent such as (2S,3S)-dibenzoyltartaric acid ((2S,3S)-DBTA) or (2S,3S)-di-4-toluoyl-tartaric acid ((2S,3S)-DTTA).
New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4
Pan, Chengqian,Shi, Yutong,Chen, Xuegang,Chen, Chen-Tung Arthur,Tao, Xinyi,Wu, Bin
, p. 1155 - 1163 (2017)
Three new quinazoline derivatives (1-3), one new oxepin-containing natural product (4) and four new cyclopenin derivatives (5-7 and 9) have been isolated from an EtOAc extract of the Taiwan Kueishantao hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4. Their planar structures were established by HRMS, 1D and 2D NMR spectroscopic data analyses. The absolute configurations for compounds 1 and 4 were determined by chiral phase HPLC analysis of their hydrolysis products. The absolute configurations of 2, 3 and 7 were defined mainly by comparison of the quantum chemical TDDFT calculated and the experimental ECD spectra, and the absolute configuration of 5 was deduced from comparison of the optical rotation values reported in the literature. The presence of two atropisomers of 5 was established by NOE analyses. The Ile & Val units in compounds 1-3 allowed the assignment of a new quinazoline skeleton and it's the first time the configuration of isoleucine in the quinazoline skeleton was defined. A series of 7-methoxy cyclopenin derivatives were reported for the first time in this study. The bioevaluation of compounds 5, 7, 8 and 9 revealed inhibitory activities against E. coli at MIC values around 32 μg mL?1
Polyketides, diketopiperazines and an isochromanone from the marine-derived fungal strain Fusarium graminearum FM1010 from Hawaii
Cao, Shugeng,Sarotti, Ariel M.,Uz Zaman, KH Ahammad,Wu, Xiaohua
, (2022/03/09)
The fungal strain Fusarium graminearum FM1010 was isolated from a shallow-water volcanic rock known as “live rock” at the Carl Smith Beach, Hilo, Hawaii. Eleven specialised metabolites, including two undescribed diketopiperazines, three undescribed polyketides, and one undescribed isochromanone, along with five known fusarielin derivatives were obtained from F. graminearum FM1010. The structures of the six undescribed compounds were elucidated by extensive analysis of NMR spectroscopy, HRESIMS, chemical reactions, and electronic circular dichroism (ECD) data. Kaneoheoic acids G-I showed mild inhibitory activity against S. aureus with the MIC values in the range of 20–40 μg/mL when assayed in combination with chloramphenicol (half of the MIC, 1 μg/mL), an FDA approved antibiotic. Kaneoheoic acid I exhibited both anti-proliferative activity against ovarian cancer cell line A2780 and TNF-α induced NF-κB inhibitory activity with the IC50 values of 18.52 and 15.86 μM, respectively.
Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
Inada, Haruki,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 709 - 713 (2019/01/25)
A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are resolvable by aminoacylases with almost complete selectivity.
D - [...] manufacturing method
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Paragraph 0040, (2018/06/12)
Provided is a method for producing D-alloisoleucine in a fewer steps and with high yield by an asymmetric transformation reaction of L-isoleucine. A method for producing D-alloisoleucine, involving a step of allowing a tartaric acid derivative represented by general formula (1) (wherein n R's independently represent a hydrogen atom, a C1-6 alkyl group, a C1-6 alkoxy group, a chlorine atom, a bromine atom or a nitro group; and n represents 0, 1 or 2) to exist in a specific reaction system in which L-isoleucine and D-alloisoleucine can be epimerized to each other, thereby causing a complex of D-alloisoleucine and the tartaric acid derivative to be crystallized.
