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CAS 209252-17-5

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Fmoc-L-beta-glutamic acid 5-tert-butyl ester

Description:
Fmoc-L-beta-glutamic acid 5-tert-butyl ester is a derivative of glutamic acid, characterized by the presence of a fluorenylmethoxycarbonyl (Fmoc) protecting group and a tert-butyl ester at the 5-position of the beta-glutamic acid structure. This compound is typically used in peptide synthesis, particularly in solid-phase peptide synthesis, due to the stability of the Fmoc group under basic conditions, which allows for selective deprotection. The tert-butyl ester enhances the lipophilicity of the molecule, facilitating its incorporation into various organic reactions. The presence of the beta-carboxylic acid group contributes to its acidic properties, while the amino group provides basic characteristics, making it an amphoteric compound. Fmoc-L-beta-glutamic acid 5-tert-butyl ester is often utilized in the synthesis of peptides that require specific stereochemistry and functional group protection, making it valuable in pharmaceutical and biochemical research. Its molecular structure allows for versatility in modifications, which is essential for developing bioactive compounds.
Formula:C24H27NO6
InChI:InChI=1/C24H27NO6/c1-24(2,3)31-22(28)13-15(12-21(26)27)25-23(29)30-14-20-18-10-6-4-8-16(18)17-9-5-7-11-19(17)20/h4-11,15,20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t15-/m1/s1
SMILES:CC(C)(C)OC(=O)C[C@@H](CC(=O)O)N=C(O)OCC1c2ccccc2c2ccccc12
Synonyms:
  • Fmoc-L-beta-homoaspartic acid 5-tert-butyl ester
  • Fmoc-beta-Glu(OtBu)-OH
  • (3R)-5-tert-butoxy-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-5-oxopentanoic acid
  • Fmoc-β-HoAsp(OtBu)-OH
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