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

Base Information

• Chemical Name: (2S,3R)-(+)-2-Amino-3-hydroxy-4-methylpentanoic acid
• CAS No.: 10148-71-7
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• Hs Code.: 29224985
• Mol file: 10148-71-7.mol

Synonyms:L-Leucine,3-hydroxy-, threo-;Leucine, 3-hydroxy-, L-threo- (8CI);(2S,3R)-3-Hydroxyleucine;L-threo-3-Hydroxyleucine;L-threo-b-Hydroxyleucine;NSC 524546;threo-3-Hydroxy-L-leucine;

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

Chemical Property:

• Appearance/Colour: white fluffy powder
• Vapor Pressure: 2.87E-05mmHg at 25°C
• Melting Point: 225-227 °C
• Refractive Index: 1.495
• Boiling Point: 318.996 °C at 760 mmHg
• PKA: 2.40±0.25(Predicted)
• Flash Point: 146.724 °C
• PSA: 83.55000
• Density: 1.181 g/cm³
• LogP: 0.11550
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3R)-(+)-2-amino-3-hydroxy-4-methylpentanoicacid 95 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25-olubility-Solubility-S24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3R)-β-Hydroxyleucine is a nonprotein amino acid. (2S,3R)-β-Hydroxyleucineis an inhibitor of serine protease. In particular, (2S,3R)-β-Hydroxyleucine was effective in inhibiting trypsin and protein ase K of the serine proteases group. (2S,3R)-β-Hydroxyleucine is able to inhibit the growth of gram-positive and gram-negative bacteria and yeasts unlike its (2R,3S)-isomer.

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

There total 51 articles about (2S,3R)-(+)-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: 66.0%

(2S,3R)-3-formyloxy-4-methyl-2-trifluoroacetamido pentan-1-oic acid → (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 potassium hydroxide; Dowex H⁺; 1.) 100 deg C, 5 h; 2.) r.t., (pH=4) then 80 deg C, 5 min;

DOI:10.1016/0040-4020(95)00024-3

upstream raw materials:

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

N-Benzyl-DL-erythro-β-hydroxy-leucin

isobutyraldehyde

glycine

Downstream raw materials:

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

(2S,3S)-3-hydroxyleucine

D,L-erythro β-Hydroxyleucine

rac-erythro-3-Hydroxyleucin-N-sulfamat Natriumsalz

Refernces

• 1、 Kumar, Prasanth,Meza, Anthony,Ellis, Jonathan M.,Carlson, Grace A.,Bingman, Craig A.,Buller, Andrew R.. "L -Threonine Transaldolase Activity Is Enabled by a Persistent Catalytic Intermediate". . p. 86 - 95. Retrieved 2021/01/09.
• 2、 Hibi, Makoto,Kasahara, Takuya,Kawashima, Takashi,Yajima, Hiroko,Kozono, Shoko,Smirnov, Sergey V.,Kodera, Tomohiro,Sugiyama, Masakazu,Shimizu, Sakayu,Yokozeki, Kenzo,Ogawa, Jun. "Multi-enzymatic synthesis of optically pure β-hydroxy α-amino acids". . p. 767 - 774. Retrieved 2015/03/18.