21704-86-9Relevant articles and documents
An organocatalyzed enantioselective synthesis of (2S,3R,4S)-4- hydroxyisoleucine and its stereoisomers
Kumaraswamy, Gullapalli,Jayaprakash, Neerasa,Sridhar, Balasubramanian
, p. 2745 - 2747 (2010)
A concise enantioselective total synthesis of (2S,3R,4S)-4- hydroxyisoleucine and its stereoisomers is described. A key feature of this protocol is a catalytic enantioselective mannich reaction that is either anti- or syn-selective as genesis of chirality.
New synthetic routes toward enantiopure (2S,3R,4R)-4-hydroxyisoleucine by 1,3-dipolar cycloaddition of a chiral nitrone to C4 alkenes
Aouadi, Kaiss,Jeanneau, Erwann,Msaddek, Moncef,Praly, Jean-Pierre
, p. 3399 - 3405 (2007)
1,3-Dipolar cycloaddition reaction of a chiral nitrone derived from (-)-menthone to E/Z mixtures of crotonaldehyde or (Z)-but-2-en-1,4-diol opens, by simultaneous creation of three contiguous asymmetric centers, new access to enantiopure (2S,3R,4R)-4-hydroxyisoleucine, respectively in 13% (7 steps) and 34% (6 steps) overall yield. Georg Thieme Verlag Stuttgart.
1,3-Dipolar cycloaddition of a chiral nitrone to (E)-1,4-dichloro-2-butene: A new efficient synthesis of (2S,3S,4R)-4-hydroxyisoleucine
Aouadi, Ka?ss,Jeanneau, Erwann,Msaddek, Moncef,Praly, Jean-Pierre
, p. 2817 - 2821 (2012)
1,3-Dipolar cycloaddition of a chiral nitrone derived from (-)-menthone to (E)-1,4-dichlorobut-2-ene was the key step in a novel 5 step synthesis of (2S,3S,4R)-4-hydroxyisoleucine, obtained in 21% overall yield with high enantiopurity.
Attempt to simultaneously generate three chiral centers in 4-hydroxyisoleucine with microbial carbonyl reductases
Hibi, Makoto,Takahashi, Koji,Kako, Junko,Wakita, Yuuta,Kodera, Tomohiro,Shimizu, Sakayu,Yokozeki, Kenzo,Ogawa, Jun
, p. 1327 - 1332 (2017/10/05)
A panel of microorganisms was screened for selective reduction ability towards a racemic mixture of prochiral 2-amino-3-methyl-4-ketopentanoate (rac-AMKP). Several of the microorganisms tested produced greater than 0.5 mM 4-hydroxyisoleucine (HIL) from rac-AMKP, and the stereoselectivity of HIL formation was found to depend on the taxonomic category to which the microorganism belonged. The enzymes responsible for the AMKP-reducing activity, ApAR and FsAR, were identified from two of these microorganisms, Aureobasidium pullulans NBRC 4466 and Fusarium solani TG-2, respectively. Three AMKP reducing enzymes, ApAR, FsAR, and the previously reported BtHILDH, were reacted with rac-AMKP, and each enzyme selectively produced a specific composition of HIL stereoisomers. The enzymes appeared to have different characteristics in recognition of the stereostructure of the substrate AMKP and in control of the 4-hydroxyl group configuration in the HIL product.