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CAS 884880-39-1

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N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-D-valine

Description:
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-D-valine, commonly referred to as Fmoc-D-HyVal, is a derivative of the amino acid D-valine, modified with a fluorenylmethoxycarbonyl (Fmoc) protecting group. This compound is characterized by its role in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS), where the Fmoc group serves as a temporary protective group for the amino functionality. The presence of the hydroxy group at the 3-position of the valine side chain enhances its solubility and can influence the conformational properties of peptides. Fmoc-D-HyVal is typically a white to off-white solid, and it is soluble in organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. Its stability under basic conditions makes it suitable for various synthetic applications. Additionally, the compound's structure allows for specific interactions in biological systems, making it of interest in medicinal chemistry and drug design.
Formula:C20H21NO5
InChI:InChI=1S/C20H21NO5/c1-20(2,25)17(18(22)23)21-19(24)26-11-16-14-9-5-3-7-12(14)13-8-4-6-10-15(13)16/h3-10,16-17,25H,11H2,1-2H3,(H,21,24)(H,22,23)/t17-/m0/s1
InChI key:InChIKey=KIOMNBRJPAICIT-KRWDZBQOSA-N
SMILES:C(OC(N[C@H](C(C)(C)O)C(O)=O)=O)C1C=2C(C=3C1=CC=CC3)=CC=CC2
Synonyms:
  • N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-D-valine
  • D-Valine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-3-hydroxy-
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