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CAS 200124-22-7

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Boc-Arg(Pbf)-OH

Description:
Boc-Arg(Pbf)-OH, also known as N-tert-butoxycarbonyl-L-arginine (Pbf refers to the 2,2,4,4,5,5-hexamethyl-3-oxazolidinyl) is a protected form of the amino acid arginine, commonly used in peptide synthesis. The Boc (tert-butoxycarbonyl) group serves as a protective group for the amino group, allowing for selective reactions without interfering with the amino functionality. The Pbf group is a bulky protecting group for the side chain guanidino group of arginine, which helps to prevent unwanted side reactions during synthesis. This compound is typically white to off-white in appearance and is soluble in organic solvents like dimethylformamide (DMF) and dimethyl sulfoxide (DMSO), but less soluble in water. It is stable under acidic conditions but can be deprotected under basic conditions or through specific reagents. Boc-Arg(Pbf)-OH is widely utilized in the field of peptide chemistry for the synthesis of peptides and proteins, particularly in solid-phase peptide synthesis, due to its ability to facilitate the formation of peptide bonds while maintaining the integrity of the arginine side chain.
Formula:C24H38N4O7S
InChI:InChI=1/C24H38N4O7S/c1-13-14(2)19(15(3)16-12-24(7,8)34-18(13)16)36(32,33)28-21(25)26-11-9-10-17(20(29)30)27-22(31)35-23(4,5)6/h17H,9-12H2,1-8H3,(H,27,31)(H,29,30)(H3,25,26,28)/t17-/m0/s1
SMILES:Cc1c(C)c(c(C)c2CC(C)(C)Oc12)S(=O)(=O)NC(=N)NCCC[C@@H](C(=O)O)N=C(O)OC(C)(C)C
Synonyms:
  • (E)-N5-(amino{[(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)sulfonyl]amino}methylidene)-N2-(tert-butoxycarbonyl)-L-ornithine
  • Z-D-Asn(Trt)
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