N-Methyl-L-leucine hydrochloride (BAT-004074)
* For research use only

Category
L-Amino Acids
Catalog number
BAT-004074
CAS number
3060-46-6
Molecular Formula
C7H15NO2·HCl
Molecular Weight
181.60
N-Methyl-L-leucine hydrochloride
Synonyms
N-Me-L-Leu-OH HCl; H-NMe-Leu-OH; H-(ME)LEU-OH; N-ME-LEUCINE; N-ME-LEU-OH; L-N-Methylleucine
Appearance
White to off-white powder
Purity
98-102% (Assay by titration)
Density
0.979±0.06 g/cm3
Melting Point
300 °C
Boiling Point
226.1±23.0 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C7H15NO2/c1-5(2)4-6(8-3)7(9)10/h5-6,8H,4H2,1-3H3,(H,9,10)/t6-/m0/s1
InChI Key
XJODGRWDFZVTKW-LURJTMIESA-N
Canonical SMILES
CC(C)CC(C(=O)O)NC
1.Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution.
Jou G1, González I, Albericio F, Lloyd-Williams P, Giralt E. J Org Chem. 1997 Jan 24;62(2):354-366.
New total syntheses of didemnin A and of dehydrodidemnin B are described. The latter didemnin has the highest antiproliferative activity of all members of this family of macrocyclic depsipeptides. It was produced on coupling the side chain Pyr-Pro-OH to didemnin A, which was itself synthesized by two novel routes. One of these was based on the elaboration of a linear heptadepsipeptide incorporating the first amino acid of the didemnin side chain, (R)-N(Me)-Leu. Deprotection of the amino and carboxyl terminii of this linear precursor followed by macrocyclization gave a protected derivative of didemnin A. The second route involved synthesis of the Boc-protected didemnin macrocycle from a linear hexadepsipeptide lacking (R)-N(Me)-Leu. Removal of the Boc group from the macrocycle followed by its coupling with Boc-(R)-N(Me)-Leu-OH then gave Boc-didemnin A. The overall yield was much higher for the second strategy (27% compared to 4% for the first synthesis), but both allowed synthetic didemnin A, identical with a natural sample, to be prepared.
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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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