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CAS 133906-29-3

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N-alpha-tert-butyloxycarbonyl-glutamic acid beta-fluorenylmethyl ester

Description:
N-alpha-tert-butyloxycarbonyl-glutamic acid beta-fluorenylmethyl ester, commonly referred to as Boc-Glu(Flu)-OH, is a protected form of glutamic acid used primarily in peptide synthesis. This compound features a tert-butyloxycarbonyl (Boc) protecting group at the alpha-amino position, which enhances the stability and solubility of the amino acid during synthetic procedures. The beta-fluorenylmethyl ester (Fm) group at the carboxylic acid position provides additional protection and facilitates the formation of peptide bonds. This compound is typically a white to off-white solid and is soluble in organic solvents such as dichloromethane and dimethylformamide, but less soluble in water. Its structure allows for selective deprotection under mild conditions, making it valuable in the synthesis of complex peptides and proteins. The presence of the fluorenylmethyl group also aids in purification processes, such as chromatography. Overall, Boc-Glu(Flu)-OH is an important intermediate in the field of organic and medicinal chemistry, particularly in the development of pharmaceuticals.
Formula:C24H27NO6
InChI:InChI=1/C24H27NO6/c1-24(2,3)31-23(29)25-20(12-13-21(26)27)22(28)30-14-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,19-20H,12-14H2,1-3H3,(H,25,29)(H,26,27)/t20-/m0/s1
InChI key:KSYVYHUPZNONJS-FQEVSTJZSA-N
SMILES:CC(C)(C)OC(=N[C@@H](CCC(=O)O)C(=O)OCC1c2ccccc2c2ccccc12)O
Synonyms:
  • BG-beta-Fme
  • Nalpha-Boc-glu-beta-fluorenylmethyl ester
  • L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 1-(9H-fluoren-9-ylmethyl) ester
  • (4S)-4-[(tert-butoxycarbonyl)amino]-5-(9H-fluoren-9-ylmethoxy)-5-oxopentanoic acid (non-preferred name)
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