(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid

Base Information

• Chemical Name: (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid
• CAS No.: 87421-23-6
• Molecular Formula: C6H13 N O3
• Molecular Weight: 147.174
• Hs Code.: 2922509090
• DSSTox Substance ID: DTXSID00369265
• Nikkaji Number: J603.007F
• Wikidata: Q72437878
• Mol file: 87421-23-6.mol

Synonyms:87421-23-6;(2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid;D-Leucine, 3-hydroxy-, (3S)-;D(-)-threo-3-Hydroxyleucine;(2R,3S)-(-)-2-Amino-3-hydroxy-4-methylpentanoic acid;35016-62-7;(2R,3S)-rel-2-Amino-3-hydroxy-4-methylpentanoic acid;D-threo-hydroxyleucine;(3S)-3-Hydroxy-D-leucine;(2R,3S)-|A-Hydroxyleucine;MFCD00142970;(d)3-hydroxy-Leucine;starbld0019666;SCHEMBL2030131;DTXSID00369265;ZAYJDMWJYCTABM-UHNVWZDZSA-N;BCP09538;AKOS016842860;AC-4459;AS-67678;A862633;(2R*,3S*)-2-amino-3-hydroxy-4-methyl-pentanoic acid;(2R,3S)-2-Amino-3-hydroxy-4-methylpentanoic acid (H-D-Leu(3S-OH)-OH)

Chemical Property of (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.87E-05mmHg at 25°C
• Melting Point: 205-208 ºC
• Refractive Index: 1.4240 (estimate)
• Boiling Point: 319 °C at 760 mmHg
• Flash Point: 146.7 °C
• PSA: 83.55000
• Density: 1.181 g/cm³
• LogP: 0.11550
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: soluble
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 124

Purity/Quality:

97% ^*data from raw suppliers

(2R,3S)-β-Hydroxyleucine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(C(=O)O)N)O
• Isomeric SMILES: CC(C)[C@@H]([C@H](C(=O)O)N)O
• Uses: (2R,3S)-β-Hydroxyleucine is a nonprotein amino acid. (2R,3S)-β-Hydroxyleucineis an inhibitor of serine protease. In particular, (2R,3S)-β-Hydroxyleucine was effective in inhibiting trypsin and proteinase K of the serine proteases group. (2R,3S)-β-Hydroxyleucine was not able to inhibit the growth of gram-positive and gram-negative bacteria and yeasts unlike its (2S,3R)-isomer.

Technology Process of (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid

There total 91 articles about (2R,3S)-2-amino-3-hydroxy-4-methylpentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

C31H33N3NiO4 → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7)

Guidance literature:

With hydrogenchloride; In methanol; for 1h; Inert atmosphere; Reflux;

DOI:10.1021/ol503507g

Reference yield: 80.0%

isobutyraldehyde (78-84-2) → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7) + (S)-2-N-(N-benzyl-L-prolyl)aminobenzophenone hydrochloride

Guidance literature:

isobutyraldehyde; Ni(II)-(S)-o-[N-(N'-benzylprolyl)amino]benzophenone/glycine Schiff base complex; With sodium hydride; In tetrahydrofuran; at 16 ℃; for 0.166667h;

With hydrogenchloride; In methanol; Heating;

DOI:10.1016/S0957-4166(01)00071-4

Reference yield: 42.0%

L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + isobutyraldehyde (78-84-2) → (2S,3R)-3-hydroxyleucine (5817-22-1,6645-45-0,10148-70-6,28908-11-4,35016-54-7,35016-62-7,87421-23-6,87421-24-7,10148-71-7) + (2S,3S)-3-hydroxyleucine (10148-70-6)

Guidance literature:

With L-threonine transaldolase; In methanol; at 37 ℃; for 18h; pH=8.5; diastereoselective reaction; Enzymatic reaction;

DOI:10.1002/cbic.202100577

upstream raw materials:

(+/-)-erythro-2-bromo-3-hydroxy-4-methyl-valeric acid

N-Benzyl-DL-erythro-β-hydroxy-leucin

isobutyraldehyde

glycine

Downstream raw materials:

(+/-)-erythro-2-benzamino-3-hydroxy-4-methyl-valeric acid

rac-threo-3-Hydroxyleucin-N-sulfamat Natriumsalz

(2S,3S)-3-hydroxyleucine

D,L-erythro β-Hydroxyleucine