N-Benzyl-D-methionine methyl ester hydrochloride
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N-Benzyl-D-methionine methyl ester hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-001587
CAS number
1272755-12-0
Molecular Formula
C13H19NO2S·HCl
Molecular Weight
289.80
IUPAC Name
methyl (2R)-2-(benzylamino)-4-methylsulfanylbutanoate;hydrochloride
Synonyms
Bzl-D-Met-OMe HCl; (R)-Methyl 2-(benzylamino)-4-(methylthio)butanoate hydrochloride
Appearance
White crystalline powder
Purity
≥ 99% (HPLC)
Melting Point
90-96°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H19NO2S.ClH/c1-16-13(15)12(8-9-17-2)14-10-11-6-4-3-5-7-11;/h3-7,12,14H,8-10H2,1-2H3;1H/t12-;/m1./s1
InChI Key
PELBNOHMQZOBAL-UTONKHPSSA-N
Canonical SMILES
COC(=O)C(CCSC)NCC1=CC=CC=C1.Cl
1. Methyl N-(3-cyano-picolino-yl)-l-tryptophanate
Olga Ovdiichuk, Olga Hordiyenko, Zoia Voitenko, Axelle Arrault, Volodymyr Medviediev Acta Crystallogr Sect E Struct Rep Online. 2013 Nov 23;69(Pt 12):o1810. doi: 10.1107/S160053681303153X.
In the title compound, C19H16N4O3, the stereocenter has an l configuration; l-tryptophan methyl ester hydro-chloride being used as a starting material. The indole ring system and the pyridine ring are inclined to one another by 13.55 (14)°. In the crystal, adjacent mol-ecules are linked via N-H⋯O hydrogen bonds, forming chains propagating along the c-axis direction.
2. Asymmetric Total Synthesis of Griseofamine B and Its Three Stereoisomers
Tao Sheng, Caiyun Ma, Guangyan Zhang, Xuan Pan, Zhanzhu Liu J Nat Prod. 2022 Apr 22;85(4):1128-1133. doi: 10.1021/acs.jnatprod.2c00069. Epub 2022 Mar 3.
The first total synthesis of griseofamine B is described starting from l-4-bromo tryptophan methyl ester hydrochloride via five steps and in 18% overall yield. Its three stereoisomers were also synthesized following the same procedure with the yields of 5%, 19%, and 5%, respectively. In vitro antibacterial activities were also evaluated. All four compounds exhibited less potent activity than griseofamine A.
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