Boc-L-threonine methyl ester
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Boc-L-threonine methyl ester

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Category
BOC-Amino Acids
Catalog number
BAT-002813
CAS number
79479-07-5
Molecular Formula
C10H19NO5
Molecular Weight
233.26
Boc-L-threonine methyl ester
IUPAC Name
methyl (2S,3R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
Synonyms
Boc-L-Thr-Ome; (2S,3R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate
Appearance
Light yellow transparent oil
Purity
≥ 98% (HPLC)
Density
1.123±0.06 g/cm3(Predicted)
Boiling Point
206 °C(lit.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H19NO5/c1-6(12)7(8(13)15-5)11-9(14)16-10(2,3)4/h6-7,12H,1-5H3,(H,11,14)/t6-,7+/m1/s1
InChI Key
MZMWAPNVRMDIPS-RQJHMYQMSA-N
Canonical SMILES
CC(C(C(=O)OC)NC(=O)OC(C)(C)C)O
1.Enzymatic Synthesis of Galactosylated Serine/Threonine Derivatives by β-Galactosidase from Escherichia coli.
Seo S1, Rebehmed J2, de Brevern AG3, Karboune S4. Int J Mol Sci. 2015 Jun 15;16(6):13714-28. doi: 10.3390/ijms160613714.
The transgalactosylations of serine/threonine derivatives were investigated using β-galactosidase from Escherichia coli as biocatalyst. Using ortho-nitrophenyl-β-D-galactoside as donor, the highest bioconversion yield of transgalactosylated N-carboxy benzyl L-serine benzyl ester (23.2%) was achieved in heptane:buffer medium (70:30), whereas with the lactose, the highest bioconversion yield (3.94%) was obtained in the buffer reaction system. The structures of most abundant galactosylated serine products were characterized by MS/MS. The molecular docking simulation revealed that the binding of serine/threonine derivatives to the enzyme's active site was stronger (-4.6~-7.9 kcal/mol) than that of the natural acceptor, glucose, and mainly occurred through interactions with aromatic residues. For N-tert-butoxycarbonyl serine methyl ester (6.8%) and N-carboxybenzyl serine benzyl ester (3.4%), their binding affinities and the distances between their hydroxyl side chain and the 1'-OH group of galactose moiety were in good accordance with the quantified bioconversion yields.
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