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CAS 138774-92-2

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fmoc-N-methyl-D-alanine

Description:
Fmoc-N-methyl-D-alanine is a derivative of the amino acid alanine, characterized by the presence of a 9-fluorenylmethoxycarbonyl (Fmoc) protecting group on the amino group and a methyl group on the nitrogen atom. This compound is commonly used in peptide synthesis as a building block due to its ability to protect the amino group during the coupling reactions while allowing for the selective deprotection of the Fmoc group under mild basic conditions. The presence of the methyl group enhances the steric hindrance and can influence the conformation of peptides, potentially affecting their biological activity. Fmoc-N-methyl-D-alanine is typically a white to off-white solid and is soluble in organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. Its stability and reactivity make it a valuable intermediate in the synthesis of various peptides and peptidomimetics, contributing to research in fields such as drug development and biochemistry.
Formula:C19H19NO4
InChI:InChI=1/C19H19NO4/c1-12(18(21)22)20(2)19(23)24-11-17-15-9-5-3-7-13(15)14-8-4-6-10-16(14)17/h3-10,12,17H,11H2,1-2H3,(H,21,22)/t12-/m1/s1
SMILES:C[C@H](C(=O)O)N(C)C(=O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-N-Me-D-Ala-OH
  • N-alpha-(9-fluorenylmethyloxycarbonyl)-N-alpha-Methyl-D-alanine
  • N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-methyl-D-alanine
  • Fmoc-D-Me-Ala-OH
  • Fmoc-D-MeAla-OH
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