(R)-1-Amino-2-methylpropylphosphonic acid
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(R)-1-Amino-2-methylpropylphosphonic acid

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Category
Others
Catalog number
BAT-006619
CAS number
66254-56-6
Molecular Formula
C4H12NO3P
Molecular Weight
153.12
(R)-1-Amino-2-methylpropylphosphonic acid
IUPAC Name
[(1R)-1-amino-2-methylpropyl]phosphonic acid
Synonyms
H-ValP(O)-(OH)2; H-AMePropP(O)-(OH)2
Density
1.295g/cm3
Melting Point
272-277 °C(lit.)
Boiling Point
302.9°C at 760 mmHg
InChI
InChI=1S/C4H12NO3P/c1-3(2)4(5)9(6,7)8/h3-4H,5H2,1-2H3,(H2,6,7,8)/t4-/m1/s1
InChI Key
DGSLPJDIFKVSIB-SCSAIBSYSA-N
Canonical SMILES
CC(C)C(N)P(=O)(O)O
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. Enantioseparation of 3-Hydroxycarboxylic Acids via Diastereomeric Salt Formation by 2-Amino-1,2-diphenylethanol (ADPE) and Cinchonidine
Srinivas Chandrasekaran, Masaki Tambo, Yuta Yamazaki, Tatsuro Muramatsu, Yusuke Kanda, Takuji Hirose, Koichi Kodama Molecules. 2022 Dec 23;28(1):114. doi: 10.3390/molecules28010114.
Enantioseparation of 3-hydroxycarboxylic acids via diastereomeric salt formation was demonstrated using 2-amino-1,2-diphenylethanol (ADPE) and cinchonidine as the resolving agents. Racemic 3-hydroxy-4-phenylbutanoic acid (rac-1), 3-hydroxy-4-(4-chlorophenyl)butanoic acid (rac-2), and 3-hydroxy-5-phenylpentanoic acid (rac-3) were efficiently resolved using these resolving agents. Moreover, the successive crystallization of the less-soluble diastereomeric salt of 1 and cinchonidine using EtOH yielded pure (R)-1 · cinchonidine salt in a high yield. The crystal structures of less-soluble diastereomeric salts were elucidated and it was revealed that hydrogen bonding and CH/π interactions play an important role in reinforcing the structure of the less-soluble diastereomeric salts.
3. Synergistic Catalysis between a Dipeptide Phosphonium Salt and a Metal-Based Lewis Acid for Asymmetric Synthesis of N-Bridged [3.2.1] Ring Systems
Yuan Chen, Jiajia He, Cheng Zhuang, Zanjiao Liu, Kai Xiao, Zhishan Su, Xiaoyu Ren, Tianli Wang Angew Chem Int Ed Engl. 2022 Sep 19;61(38):e202207334. doi: 10.1002/anie.202207334. Epub 2022 Jul 25.
We present an unprecedented synergic catalytic route for the asymmetric construction of fluorinated N-bridged [3.2.1] cyclic members of tropane family via a bifunctional phosphonium salt/silver co-catalyzed cyclization process. A broad variety of substrates bearing an assortment of functional groups are compatible with this method, providing targeted compounds bearing seven-membered ring and four contiguous stereocenters in high yields with excellent stereoselectivities. The gram-scale preparations, facile elaborations and preliminary biological activities of the products demonstrate the application potential. Moreover, both experimental and computational mechanistic studies revealed that the cyclization proceeded via a "sandwich" reaction model with multiple weak-bond cooperative activations. Insights gained from our studies are expected to advance general efforts towards the catalytic synthesis of challenging chiral heterocyclic molecules.
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