(R)-2-Amino-2-methylhex-5-enoic acid
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(R)-2-Amino-2-methylhex-5-enoic acid

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Category
Amino Acids for Stapled Peptide
Catalog number
BAT-006324
CAS number
1932326-29-8
Molecular Formula
C7H13NO2
Molecular Weight
143.18
IUPAC Name
(2R)-2-amino-2-methylhex-5-enoic acid
Synonyms
(R)-2-(3'-Butenyl)alanine
Appearance
White powder
Purity
97% (HPLC)
Density
1.0±0.1 g/cm3
Boiling Point
249.7±28.0 °C at 760 mmHg
Storage
Store at RT
InChI
InChI=1S/C7H13NO2/c1-3-4-5-7(2,8)6(9)10/h3H,1,4-5,8H2,2H3,(H,9,10)/t7-/m1/s1
InChI Key
OQVMALDNOMXRAP-SSDOTTSWSA-N
Canonical SMILES
CC(CCC=C)(C(=O)O)N
1. A Vegan Diet Is Associated with a Significant Reduction in Dietary Acid Load: Post Hoc Analysis of a Randomized Controlled Trial in Healthy Individuals
Alexander Müller, Amy Marisa Zimmermann-Klemd, Ann-Kathrin Lederer, Luciana Hannibal, Stefanie Kowarschik, Roman Huber, Maximilian Andreas Storz Int J Environ Res Public Health. 2021 Sep 23;18(19):9998. doi: 10.3390/ijerph18199998.
The composition of diet strongly affects acid-base homeostasis. Western diets abundant in acidogenic foods (meat and cheese) and deficient in alkalizing foods (fruits and vegetables) increase dietary acid load (DAL). A high DAL has been associated with numerous health repercussions, including cardiovascular disease and type-2-diabetes. Plant-based diets have been associated with a lower DAL; however, the number of trials exploring this association is limited. This randomized-controlled trial sought to examine whether an isocaloric vegan diet lowers DAL as compared to a meat-rich diet. Forty-five omnivorous individuals were randomly assigned to a vegan diet (n = 23) or a meat-rich diet (n = 22) for 4 weeks. DAL was determined using potential renal acid load (PRAL) and net endogenous acid production (NEAP) scores at baseline and after 3 and 4 weeks, respectively. After 3 weeks, median PRAL (-23.57 (23.87)) and mean NEAPR (12.85 ± 19.71) scores were significantly lower in the vegan group than in the meat-rich group (PRAL: 18.78 (21.04) and NEAPR: 60.93 ± 15.51, respectively). Effects were mediated by a lower phosphorus and protein intake in the vegan group. Our study suggests that a vegan diet is a potential means to reduce DAL, whereas a meat-rich diet substantially increases the DAL burden.
2. Engineering robust microorganisms for organic acid production
Vinh G Tran, Huimin Zhao J Ind Microbiol Biotechnol. 2022 Apr 14;49(2):kuab067. doi: 10.1093/jimb/kuab067.
Organic acids are an important class of compounds that can be produced by microbial conversion of renewable feedstocks and have huge demands and broad applications in food, chemical, and pharmaceutical industries. An economically viable fermentation process for production of organic acids requires robust microbial cell factories with excellent tolerance to low pH conditions, high concentrations of organic acids, and lignocellulosic inhibitors. In this review, we summarize various strategies to engineer robust microorganisms for organic acid production and highlight their applications in a few recent examples.
3. Towards the biodegradation pathway of fosfomycin
K Pallitsch, A Schweifer, A Roller, F Hammerschmidt Org Biomol Chem. 2017 Apr 11;15(15):3276-3285. doi: 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.
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