D-Leucine methyl ester hydrochloride

white crystalline powder

According to S.G. Davies, H.J. Sanganee, P. Szolcsanyl, Tetrahedron 55 (1999) 3337 as follows: Chosen amino acid (d‑leucine (60.24 mmol)) was suspended in anhydrous MeOH (100 mL) and cooled to 0 °C in an ice/salt bath. Thionyl chloride (SOClD-Leucine (3.00 g, 22.9 mmol) was added to a solution of acetyl chloride (1.70 mL, 23.9 mmol) in methanol (30 mL). The reaction mixture was allowed to stir for 18 h and then concentrated under reduced pressure. This yielded 3.8 g (91percent) of the title compound. General procedure: To a suspension of 5 g of D-amino acid in 100 mLdry methanol at 0–5°, 8–10 mL thionyl chloridewere added dropwise, the mixture was stirred for 2 hand kept at 20–22° for 24 h. The solvent was evaporatedunder vacuum at 30–40°, the residue wasmixed with dry ether, filtered off, dried, and recrystallizedfrom methanol–ether mixture.

D-Leucine methyl ester hydrochloride is a protected form of D-Leucine (L330150). D-Leucine is an unnatural isomer of L-Leucine (L330110) that acts as an auto-inhibitor of lactic streptococci in culture. D-Leucine causes analgesia in humans and also exhibits inhibitory activity in bacterial cell cultures.

Molecular Weight:181.66
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:181.0869564
Monoisotopic Mass:181.0869564
Topological Polar Surface Area:52.3
Heavy Atom Count:11
Complexity:112
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes