(R)-4-Acetamido-5-hydroxypentanoic acid

(R)-4-Acetamido-5-hydroxypentanoic acid

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(R)-4-Acetamido-5-hydroxypentanoic acid
Category Others
Catalog number BBF-04772
CAS
Molecular Weight 175.2
Molecular Formula C7H13NO4

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Reference Reading

1. Chiral Phosphoric Acid Catalyzed Enantioselective Desymmetrization of 1,4-Dihydropyridines by C(sp3 )-H Bromination
Min Han, Shi-Qi Zhang, Xin Cui, Qi-Wei Wang, Guang-Xun Li, Zhuo Tang Angew Chem Int Ed Engl. 2022 May 23;61(22):e202201418. doi: 10.1002/anie.202201418. Epub 2022 Mar 31.
Described herein is the enantioselective synthesis of Hantzsch-type 1,4-dihydropyridines (DHPs), which are frequently contained in pharmaceuticals. Readily available symmetrical 1,4-DHPs were used as substrates, and the methyl group at the 2- or 6-position of the 1,4-DHP was selectively monobrominated by desymmetrizing enantioselective bromination. The inert C-H bond was converted into a versatile C-Br bond, which guaranteed the modification of the chiral 1,4-DHP derivatives with high efficiency. Furthermore, axially chiral 4-aryl pyridines were accessible by central-to-axial chirality conversion.
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. New Gelatin-Based Hydrogel Foams for Improved Substrate Conversion of Immobilized Horseradish Peroxidase
Friederike Dehli, Cosima Stubenrauch, Alexander Southan Macromol Biosci. 2022 Sep;22(9):e2200139. doi: 10.1002/mabi.202200139. Epub 2022 Jul 13.
Hydrogel foams provide an aqueous environment that is very attractive for the immobilization of enzymes. To this end, functional polymers are needed that can be converted into hydrogel foams and that enable bioconjugation while maintaining high enzyme activity. The present study demonstrates the potential of biotinylated gelatin methacryloyl (GM10EB) for this purpose. GM10EB is synthesized in a two-step procedure with gelatin methacryloyl (GM10) being the starting point. Successful biotinylation is confirmed by 2,4,6-trinitrobenzene sulfonic acid and 4'-hydroxyazobenzene-2-carboxylic acid/avidin assays. Most importantly, a high methacryloyl group content (DM) is maintained in GM10EB, so that solutions of GM10EB show both a sufficiently low viscosity for microfluidic foaming and a pronounced curing behavior. Thus, foamed and nonfoamed GM10EB hydrogels can be prepared via radical crosslinking of the polymer chains. Within both sample types, biotin groups are available for bioconjugation, as is demonstrated by coupling streptavidin-conjugated horseradish peroxidase to the hydrogels. When assessing the substrate conversion rate rA in foamed hydrogels by enzymatic conversion of 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), a value for rA 12 times higher than the value for nonfoamed hydrogels of the same mass is observed. In other words, rA can be successfully tailored by the hydrogel morphology.

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