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(R)-2-formamido-4-methylpentanoic acid

(Synonyms: 赖氨酸杂质12) 目录号 : GC68102

(R)-2-formamido-4-methylpentanoic acid 是一种亮氨酸衍生物。

(R)-2-formamido-4-methylpentanoic acid Chemical Structure

Cas No.:44978-39-4

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250mg
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产品描述

(R)-2-formamido-4-methylpentanoic acid is a leucine derivative[1].

Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. They influence the secretion of anabolic hormones, supply of fuel during exercise, mental performance during stress related tasks and prevent exercise induced muscle damage. They are recognized to be beneficial as ergogenic dietary substances[1].

[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Chemical Properties

Cas No. 44978-39-4 SDF Download SDF
别名 赖氨酸杂质12
分子式 C7H13NO3 分子量 159.18
溶解度 DMSO : 100 mg/mL (628.22 mM; Need ultrasonic) 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 6.2822 mL 31.411 mL 62.822 mL
5 mM 1.2564 mL 6.2822 mL 12.5644 mL
10 mM 0.6282 mL 3.1411 mL 6.2822 mL
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Research Update

Structure of 4-carboxy-2-nitrobenzeneboronic acid

Acta Crystallogr C 1993 Apr 15;49 ( Pt 4):690-3.PMID:8494629DOI:10.1107/s0108270192010916.

4-(Dihydroxyboryl)-3-nitrobenzoic acid, C7H6BNO6, M(R) = 210.94, monoclinic, P2(1)/n, a = 10.542 (2), b = 6.411 (1), c = 13.105 (4) A, beta = 106.47 (2) degrees, V = 849.3 (4) A3, Z = 4, Dm = 1.65 (flotation in CCl4/1,2-dibromoethane), Dx = 1.649 Mg m-3, lambda(Mo K alpha) = 0.71073 A, mu = 0.135 mm-1, F(000) = 432, T = 293 K, R = 0.0530 for 1328 observed reflections with F > 2 sigma(F). The molecule is flat [the carboxy and nitro groups are rotated 5.8 (4) and 1.9 (4) degrees, respectively, out of the plane] with the boronic acid group almost normal to the plane of the benzene ring, 92.4 (3) degrees. The B atom and one O atom of the nitro group are separated by only 2.457 (4) A implying an interaction that is consistent with observed chemical behavior.

Towards the biodegradation pathway of fosfomycin

Org Biomol Chem 2017 Apr 11;15(15):3276-3285.PMID:28352915DOI:10.1039/c7ob00546f.

Three functionalised propylphosphonic acids were synthesised to study C-P bond cleavage in R. huakuii PMY1. (R)-1-Hydroxy-2-oxopropylphosphonic acid [(R)-5] was prepared by chiral resolution of (±)-dimethyl 1-hydroxy-2-methylallyllphosphonate [(±)-12], followed by ozonolysis and deprotection. The N-(l-alanyl)-substituted (1R,2R)-2-amino-1-hydroxypropylphosphonic acid 10, a potential precursor for 2-oxopropylphosphonic acid (5) in cells, was obtained by coupling the aminophosphonic acid with benzotriazole-activated Z-l-alanine and hydrogenolytic deprotection. (1R*,2R*)-1,2-Dihydroxy-3,3,3-trifluoropropylphosphonic acid, a potential inhibitor of C-P bond cleavage after conversion into its 2-oxo derivative in the cell, was accessed from trifluoroacetaldehyde hydrate via hydroxypropanenitrile 21, which was silylated and reduced to the aldehyde (±)-23. Diastereoselective addition of diethyl trimethylsilyl phosphite furnished diastereomeric α-siloxyphosphonates. The less polar one was converted to the desired racemic phosphonic acid (±)-(1R*,2R*)-9 as its ammonium salt.

Adaptive response and tolerance to weak acids in Saccharomyces cerevisiae: a genome-wide view

OMICS 2010 Oct;14(5):525-40.PMID:20955006DOI:10.1089/omi.2010.0072.

Weak acids are widely used as food preservatives (e.g., acetic, propionic, benzoic, and sorbic acids), herbicides (e.g., 2,4-dichlorophenoxyacetic acid), and as antimalarial (e.g., artesunic and artemisinic acids), anticancer (e.g., artesunic acid), and immunosuppressive (e.g., mycophenolic acid) drugs, among other possible applications. The understanding of the mechanisms underlying the adaptive response and resistance to these weak acids is a prerequisite to develop more effective strategies to control spoilage yeasts, and the emergence of resistant weeds, drug resistant parasites or cancer cells. Furthermore, the identification of toxicity mechanisms and resistance determinants to weak acid-based pharmaceuticals increases current knowledge on their cytotoxic effects and may lead to the identification of new drug targets. This review integrates current knowledge on the mechanisms of toxicity and tolerance to weak acid stress obtained in the model eukaryote Saccharomyces cerevisiae using genome-wide approaches and more detailed gene-by-gene analysis. The major features of the yeast response to weak acids in general, and the more specific responses and resistance mechanisms towards a specific weak acid or a group of weak acids, depending on the chemical nature of the side chain R group (R-COOH), are highlighted. The involvement of several transcriptional regulatory networks in the genomic response to different weak acids is discussed, focusing on the regulatory pathways controlled by the transcription factors Msn2p/Msn4p, War1p, Haa1p, Rim101p, and Pdr1p/Pdr3p, which are known to orchestrate weak acid stress response in yeast. The extrapolation of the knowledge gathered in yeast to other eukaryotes is also attempted.

Dynamic experiments of acid mine drainage with Rhodopseudomonas spheroides activated lignite immobilized sulfate-reducing bacteria particles treatment

Sci Rep 2022 May 24;12(1):8783.PMID:35610343DOI:10.1038/s41598-022-12897-9.

Aiming at the problem that the treatment of acid mine drainage (AMD) by sulfate-reducing bacteria (SRB) biological method is susceptible to pH, metal ions, sulfate and carbon source. Lignite immobilized SRB particles (SRB-LP) and Rhodopseudomonas spheroides (R. spheroides) activated lignite immobilized SRB particles (R-SRB-LP) were prepared using microbial immobilization technology with SRB, R. spheroides and lignite as the main substrates. The dynamic experimental columns 1# and 2# were constructed with SRB-LP and R-SRB-LP as fillers, respectively, to investigate the dynamic repair effect of SRB-LP and R-SRB-LP on AMD. The mechanism of AMD treated with R-L-SRB particles was analyzed by scanning electron microscopy (SEM), fourier transform infrared (FTIR) spectrometer and low-temperature nitrogen adsorption. The result showed that the combination of R. spheroides and lignite could continuously provide carbon source for SRB, so that the highest removal rates of SO42-, Cu2+ and Zn2+ in AMD by R-SRB-LP were 93.97%, 98.52% and 94.42%, respectively, and the highest pH value was 7.60. The dynamic repair effect of R-SRB-LP on AMD was significantly better than that of SRB-LP. The characterization results indicated that after R-SRB-LP reaction, the functional groups of -OH and large benzene ring structure in lignite were broken, the lignite structure was destroyed, and the specific surface area was 1.58 times larger than before reaction. It illustrated that R. spheroides provided carbon source for SRB by degrading lignite. The strong SRB activity in R-SRB-LP, SRB can co-treat AMD with lignite, so that the dynamic treatment effect of R-SRB-LP on AMD is significantly better than that of SRB-LP.

Conclusive evidence on the mechanism of the rhodium-mediated decyanative borylation

J Am Chem Soc 2015 Sep 30;137(38):12321-9.PMID:26339861DOI:10.1021/jacs.5b07357.

The stoichiometric reactions proposed in the mechanism of the rhodium-mediated decyanative borylation have been performed and all relevant intermediates isolated and characterized including their X-ray structures. Complex RhCl{xant(P(i)Pr2)2} (1, xant(P(i)Pr2)2 = 9,9-dimethyl-4,5-bis(diisopropylphosphino)xanthene) reacts with bis(pinacolato)diboron (B2pin2), in benzene, to give the rhodium(III) derivative RhHCl(Bpin){xant(P(i)Pr2)2} (4) and PhBpin. The reaction involves the oxidative addition of B2pin2 to 1 to give RhCl(Bpin)2{xant(P(i)Pr2)2}, which eliminates ClBpin generating Rh(Bpin){xant(P(i)Pr2)2} (2). The reaction of the latter with the solvent yields PhBpin and the monohydride RhH{xant(P(i)Pr2)2} (6), which adds the eliminated ClBpin. Complex 4 and its catecholboryl counterpart RhHCl(Bcat){xant(P(i)Pr2)2} (7) have also been obtained by oxidative addition of HBR2 to 1. Complex 2 is the promoter of the decyanative borylation. Thus, benzonitrile and 4-(trifluoromethyl)benzonitrile insert into the Rh-B bond of 2 to form Rh{C(R-C6H4)═NBpin}{xant(P(i)Pr2)2} (R = H (8), p-CF3 (9)), which evolve into the aryl derivatives RhPh{xant(P(i)Pr2)2} (3) and Rh(p-CF3-C6H4){xant(P(i)Pr2)2} (10), as a result of the extrusion of CNBpin. The reactions of 3 and 10 with B2pin2 yield the arylBpin products and regenerate 2.