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CAS 942153-03-9

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(R)-4-Fmoc-3-morpholinecarboxylic acid

Description:
(R)-4-Fmoc-3-morpholinecarboxylic acid is a chiral amino acid derivative commonly used in peptide synthesis and drug development. The "Fmoc" (9-fluorenylmethoxycarbonyl) group serves as a protective group for the amino functionality, allowing for selective reactions without interfering with other functional groups. This compound features a morpholine ring, which contributes to its unique steric and electronic properties, enhancing its solubility and reactivity in various solvents. The presence of the carboxylic acid group provides acidity, making it useful in coupling reactions. Its chirality, indicated by the (R) configuration, is crucial for biological activity, as many biological systems are sensitive to the stereochemistry of amino acids. The compound is typically utilized in solid-phase peptide synthesis, where the Fmoc group can be removed under mild basic conditions, facilitating the sequential addition of amino acids. Overall, (R)-4-Fmoc-3-morpholinecarboxylic acid is a valuable building block in the synthesis of peptides and other biologically active molecules.
Formula:C20H19NO5
InChI:InChI=1S/C20H19NO5/c22-19(23)18-12-25-10-9-21(18)20(24)26-11-17-15-7-3-1-5-13(15)14-6-2-4-8-16(14)17/h1-8,17-18H,9-12H2,(H,22,23)/t18-/m1/s1
SMILES:c1ccc2c(c1)c1ccccc1C2COC(=O)N1CCOC[C@@H]1C(=O)O
Synonyms:
  • 4-Fmoc-3(R)-morpholinecarboxylic acid
  • (3R)-4-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-morpholinecarboxylic acid
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