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CAS 112898-00-7

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N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamine

Description:
N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamine, commonly referred to as Fmoc-D-glutamine, is a derivative of the amino acid D-glutamine, modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is primarily utilized in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a protective moiety for the amino group, allowing for selective deprotection and coupling reactions. The Fmoc group is known for its stability under basic conditions and can be removed under mild acidic conditions, making it advantageous for sequential amino acid addition. The presence of the D-glutamine moiety contributes to the compound's role in forming peptides with specific stereochemistry, which is crucial for biological activity. Additionally, the fluorenyl group provides a chromophore that can be utilized for monitoring reactions via UV spectroscopy. Overall, Fmoc-D-glutamine is an important building block in the synthesis of peptides and proteins in biochemical research and pharmaceutical applications.
Formula:C20H20N2O5
InChI:InChI=1S/C20H20N2O5/c21-18(23)10-9-17(19(24)25)22-20(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H2,21,23)(H,22,26)(H,24,25)/t17-/m1/s1
InChI key:InChIKey=IZKGGDFLLNVXNZ-QGZVFWFLSA-N
SMILES:C(OC(N[C@H](CCC(N)=O)C(O)=O)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2
Synonyms:
  • (2R)-5-Amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid
  • 299: PN: US20070042401 PAGE: 38 claimed protein
  • 991: PN: WO2006135786 PAGE: 71 claimed protein
  • <span class="text-smallcaps">D</span>-Glutamine, N<sup>2</sup>-[(9H-fluoren-9-ylmethoxy)carbonyl]-
  • Fmoc-D-Gln-OH
  • N<sup>2</sup>-[(9H-Fluoren-9-ylmethoxy)carbonyl]-<span class="text-smallcaps">D</span>-glutamine
  • N~2~-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-glutamine
  • N2-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamine
  • D-Glutamine, N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-
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