1509-35-9Relevant academic research and scientific papers
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).
A simple preparation of d-alloisoleucine from l-isoleucine via acetylation and separation of the ammonium salts
Yajima, Tatsuo,Horikawa, Takao,Takeda, Nobuhiro,Takemura, Eri,Hattori, Hiroaki,Shimazaki, Yuichi,Shiraiwa, Tadashi
, p. 1285 - 1287 (2008)
d-Alloisoleucine was obtained from l-isoleucine by acetylation and epimerization by acetic anhydride followed by separation of the diastereoisomeric ammonium salts using the solubility difference. The structure-solubility relationship of diastereoisomeric salts was explained by X-ray crystal structure analysis.
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
Racemisation of Activated, Urethane-protected Amino-acids by p-Dimethylaminopyridine. Significance in Solid-phase Peptide Synthesis
Atherton, Eric,Benoiton, N. Leo,Brown, Evelyn,Sheppard, Robert C.,Williams, Brian J.
, p. 336 - 337 (1981)
Racemisation of Nα-t-butoxycarbonyl, fluoren-9-ylmethoxycarbonyl, and benzyloxycarbonyl amino-acid anhydrides by p-dimethylaminopyridine is shown to be a significant side reaction during attachment of the first amino-acid to the resin in solid-phase peptide synthesis.
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.
Rational engineering ofAcinetobacter tandoiiglutamate dehydrogenase for asymmetric synthesis ofl-homoalanine through biocatalytic cascades
Diao, Shiqing,Jiang, Shuiqin,Liu, Yan,Sun, Yangyang,Wang, Hualei,Wang, Liuzhu,Wei, Dongzhi
, p. 4208 - 4215 (2021/06/30)
l-Homoalanine, a useful building block for the synthesis of several chiral drugs, is generally synthesized through biocascades using natural amino acids as cheap starting reactants. However, the addition of expensive external cofactors and the low efficiency of leucine dehydrogenases towards the intermediate 2-ketobutyric acid are two major challenges in industrial applications. Herein, a dual cofactor-dependent glutamate dehydrogenase fromAcinetobacter tandoii(AtGluDH) was identified to help make full use of the intracellular pool of cofactors when using whole-cell catalysis. Through reconstruction of the hydrophobic network between the enzyme and the terminal methyl group of the substrate 2-ketobutyric acid, the strict substrate specificity ofAtGluDH towards α-ketoglutarate was successfully changed, and the activity obtained by the most effective mutant (K76L/T180C) was 17.2 times higher than that of the wild-type protein. A three-enzyme co-expression system was successfully constructed in order to help release the mass transfer restriction. Using 1 Ml-threonine, which is close to the solubility limit, we obtained a 99.9% yield ofl-homoalanine in only 3.5 h without adding external coenzymes to the cascade, giving 99.9% ee and a 29.2 g L?1h?1space-time yield. Additionally, the activities of the engineeredAtGluDH towards some other hydrophobic amino acids were also improved to 1.1-11.2 fold. Therefore, the engineering design of some dual cofactor-dependent GluDHs could not only eliminate the low catalytic activity of unnatural substrates but also enhance the cofactor utilization efficiency of these enzymes in industrial applications.
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.
Discovery of new A- and B-type laxaphycins with synergistic anticancer activity
Cai, Weijing,Matthew, Susan,Chen, Qi-Yin,Paul, Valerie J.,Luesch, Hendrik
, p. 2310 - 2319 (2018/04/02)
Two new cyclic lipopeptides termed laxaphycins B4 (1) and A2 (2) were discovered from a collection of the marine cyanobacterium Hormothamnion enteromorphoides, along with the known compound laxaphycin A. The planar structures were solved based on a combined interpretation of 1D and 2D NMR data and mass spectral data. The absolute configurations of the subunits were determined by chiral LC-MS analysis of the hydrolysates, advanced Marfey's analysis and 1D and 2D ROESY experiments. Consistent with similar findings on other laxaphycin A- and B-type peptides, laxaphycin B4 (1) showed antiproliferative effects against human colon cancer HCT116 cells with IC50 of 1.7 μM, while laxaphycins A and A2 (2) exhibited weak activities. The two major compounds isolated from the sample, laxaphycins A and B4, were shown to act synergistically to inhibit the growth of HCT116 colorectal cancer cells.
D - [...] manufacturing method
-
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.
NMR-based assignment of isoleucine: Vs. allo -isoleucine stereochemistry
Anderson, Zoe J.,Hobson, Christian,Needley, Rebecca,Song, Lijiang,Perryman, Michael S.,Kerby, Paul,Fox, David J.
supporting information, p. 9372 - 9378 (2017/11/22)
A simple 1H and 13C NMR spectrometric analysis is demonstrated that permits differentiation of isoleucine and allo-isoleucine residues by inspection of the chemical shift and coupling constants of the signals associated with the proton and carbon at the α-stereocentre. This is applied to the estimation of epimerisation during metal-free N-arylation and peptide coupling reactions.
