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CAS 3674-06-4

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N-tert-Butyloxycarbonyl-L-phenylalanine N-hydroxysuccinimide ester

Description:
N-tert-Butyloxycarbonyl-L-phenylalanine N-hydroxysuccinimide ester, commonly referred to as Boc-L-Phe-OSu, is a chemical compound used primarily in peptide synthesis and bioconjugation. It features a tert-butyloxycarbonyl (Boc) protecting group, which is commonly employed to protect the amino group of amino acids during synthesis. The N-hydroxysuccinimide (NHS) ester functionality allows for efficient coupling reactions with amines, facilitating the formation of peptide bonds. This compound is typically a white to off-white solid and is soluble in organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. Its reactivity is characterized by the ability to form stable amide bonds upon reaction with primary or secondary amines, making it valuable in the development of peptide-based drugs and biomaterials. Additionally, the Boc group can be removed under mild acidic conditions, allowing for the subsequent deprotection of the amino group for further functionalization or incorporation into larger peptide sequences. Proper handling and storage conditions are essential due to its sensitivity to moisture and air.
Formula:C18H22N2O6
InChI:InChI=1S/C18H22N2O6/c1-18(2,3)25-17(24)19-13(11-12-7-5-4-6-8-12)16(23)26-20-14(21)9-10-15(20)22/h4-8,13H,9-11H2,1-3H3,(H,19,24)/t13-/m0/s1
InChI key:InChIKey=NHUCANAMPJGMQL-ZDUSSCGKSA-N
SMILES:O(C([C@H](CC1=CC=CC=C1)NC(OC(C)(C)C)=O)=O)N2C(=O)CCC2=O
Synonyms:
  • (2,5-Dioxopyrrolidin-1-yl) (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
  • 2,5-dioxopyrrolidin-1-yl N-(tert-butoxycarbonyl)-L-phenylalaninate
  • 29: PN: US20070066537 PAGE: 12 claimed protein
  • <span class="text-smallcaps">L</span>-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 2,5-dioxo-1-pyrrolidinyl ester
  • Alanine, N-carboxy-3-phenyl-, N-tert-butyl ester, succinimido deriv., <span class="text-smallcaps">L</span>-
  • BOC-L-Phenylalanine Osu
  • Boc-<span class="text-smallcaps">L</span>-Phe-OSu
  • Boc-Phe-OSu
  • Carbamic acid, [(1S)-2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester
  • Carbamic acid, [2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxo-1-(phenylmethyl)ethyl]-, 1,1-dimethylethyl ester, (S)-
  • See more synonyms
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