21704-86-9

Basic information

• Product Name: 4-Hydroxyisoleucine
• Synonyms: 2-Amino-2,3,5-trideoxy-3-methyl-D-xylonic Acid, (2S,3R,4S)-4-Hydroxyisoleucine Major Isomer and (2R,3R,4S)-4-Hydroxyisoleucine Minor Isomer;(2-S-3-R-4-S)Hydroxyisoleucine;4-HYDOXY-L-ISOLEUCINE
• CAS NO: 21704-86-9
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.17
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives
• Mol File: 21704-86-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: >200°C
• Boiling Point: 332°C
• Flash Point: 147°C
• Appearance: /
• Density: 1.181
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 4-Hydroxyisoleucine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyisoleucine(21704-86-9)
• EPA Substance Registry System: 4-Hydroxyisoleucine(21704-86-9)

Safety Data

• Hazardous Substances Data: 21704-86-9(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Solid

Uses

Used as a treatment for type II diabetes

InChI:InChI=1/C6H13NO3/c1-3(4(2)8)5(7)6(9)10/h3-5,8H,7H2,1-2H3,(H,9,10)/t3-,4?,5-/m0/s1

Upstream product

• 21704-91-6 (3S,4R,5S)-3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone hydrochloride 
• 600-18-0 2-Oxobutyric acid 
• 75-07-0 acetaldehyde 
• 168610-73-9 (3SR,4RS,5SR)-3-amino-4,5-dimethyldihydrofuran-2-one 
• 55527-86-1 (3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one 
• 55527-85-0 (3S,4R,5R)-3-Amino-4,5-dimethyl-dihydro-furan-2-one 
• 168610-73-9 4-hydroxyisoleucine γ-lactone 
• 1093653-23-6 C₇H₁₁NO₃ 
• 942208-47-1 C₇H₁₂N₂O₃ 
• 950204-27-0 (2R,4S,5R,6S)-5,6-dimethyl-2-(4-nitrophenyl)-tetrahydro-2H-1,3-oxazin-4-carboxylic acid 
• 950204-59-8 (2R,4S,5R,6S)-2-cyclohexyl-5,6-dimethyl-tetrahydro-2H-1,3-oxazin-4-carboxylic acid 
• 950204-60-1 (2R,4S,5R,6S)-5,6-dimethyl-2-phenyl-tetrahydro-2H-1,3-oxazin-4-carboxylic acid 
• 885054-30-8 ethyl (2S,3R)-2-amino-3-methyl-4-oxopentanoate 
• 73-32-5 L-isoleucine 

Downstream Products

• 71392-28-4 (3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one 
• 55527-86-1 (3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one 

Relevant articles and documents

An organocatalyzed enantioselective synthesis of (2S,3R,4S)-4- hydroxyisoleucine and its stereoisomers

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

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

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

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.