(R)-3-Amino-5-hexynoic acid
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(R)-3-Amino-5-hexynoic acid

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Category
β−Amino acids
Catalog number
BAT-014006
CAS number
678969-17-0
Molecular Formula
C6H9NO2
Molecular Weight
127.14
IUPAC Name
(3R)-3-aminohex-5-ynoic acid
Related CAS
332064-87-6 (hydrochloride)
Density
1.2±0.1 g/cm3
Boiling Point
274.4±35.0 °C at 760 mmHg
InChI
InChI=1S/C6H9NO2/c1-2-3-5(7)4-6(8)9/h1,5H,3-4,7H2,(H,8,9)/t5-/m1/s1
InChI Key
DWFMCQGMVSIJBN-RXMQYKEDSA-N
Canonical SMILES
C#CCC(CC(=O)O)N
1. λ3-Iodane/Lewis Acid Mediated Intramolecular Cross-Nucleophile Coupling of β-Amino Acrylates: Chemodivergent Syntheses of Indole Alkaloidal Frameworks
Zenghui Sun, Shilin Xue, Yining Zhang, Shiyang Xin, Ran Guo, Xiaowei Shi, Yan Fu, Huicai Guo, Yi Liu, Lei Wang Org Lett. 2022 Jul 29;24(29):5381-5385. doi: 10.1021/acs.orglett.2c02060. Epub 2022 Jul 17.
Herein, we report an unprecedented intramolecular cross-nucleophile coupling strategy of indole tethered β-amino acrylates using a catalyst system combining λ3-iodanes and Lewis acids to achieve the chemodivergent synthesis of three unique alkaloid skeletons. It was worth noting that the acquisition of spiroindolenines and azepino[4,5-b]indoles derivatives was switchable with choice of the Lewis acids. Moreover, the polycyclic spiroindolines containing a lactone fragment could also be accessed for the first time via cross-nucleophile coupling cascade intramolecular condensation sequence.
2. Bis-Boric Acid-Mediated Regioselective Reductive Aminolysis of 3,4-Epoxy Alcohols
Wei Tang, Chuan Wang J Org Chem. 2022 Nov 18;87(22):15653-15660. doi: 10.1021/acs.joc.2c01878. Epub 2022 Nov 3.
Herein we report a bis-boric acid-mediated regioselective reductive aminolysis of 3,4-epoxy alcohols, providing new access to prepare amino diols in high diastereofidelity directly starting from nitroarenes. Notably, this step-economical process is enabled by the essential dual function of bis-boric acid, which is engaged initially in the 4,4'-bipyridine-catalyzed reduction of nitro compounds as the reductant and subsequently promotes the ring opening reaction of 3,4-epoxy alcohols with the in situ-generated anilines.
3. 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.
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