Nα-Fmoc-Nω,Nω'-bis-Boc-L-arginine
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Nα-Fmoc-Nω,Nω'-bis-Boc-L-arginine

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Category
BOC-Amino Acids
Catalog number
BAT-004522
CAS number
143824-77-5
Molecular Formula
C31H40N4O8
Molecular Weight
596.70
Nα-Fmoc-Nω,Nω'-bis-Boc-L-arginine
Synonyms
Fmoc-L-Arg(Boc)2-OH; (S)-5-[[Bis(Boc-Amino)Methylene]Amino]-2-(Fmoc-Amino)Pentanoic Acid
Appearance
White to off-white powder
Purity
≥ 94% (HPLC)
Density
1.25±0.1 g/cm3(Predicted)
Storage
Store at-20 °C
InChI
InChI=1S/C31H40N4O8/c1-30(2,3)42-28(39)34-26(32)35(29(40)43-31(4,5)6)17-11-16-24(25(36)37)33-27(38)41-18-23-21-14-9-7-12-19(21)20-13-8-10-15-22(20)23/h7-10,12-15,23-24H,11,16-18H2,1-6H3,(H,33,38)(H,36,37)(H2,32,34,39)/t24-/m0/s1
InChI Key
QAWFIDADTYJUPT-DEOSSOPVSA-N
Canonical SMILES
CC(C)(C)OC(=O)N=C(N)N(CCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C
1.Studies on lactam formation during coupling procedures of N alpha-N omega-protected arginine derivatives.
Cezari MH1, Juliano L. Pept Res. 1996 Mar-Apr;9(2):88-91.
We evaluated the quantity of delta-lactam generated during the synthesis of arginine-containing dipeptides using Z-Arg(Tos)-OH, Boc-Arg(Tos)-OH, Fmoc-Arg(Boc)2-OH and Fmoc-Arg(Pmc)-OH and assayed several carboxyl-activating procedures for coupling the protected arginines to different amino components. We observed significant amounts of delta-lactam during the synthesis of Z-Arg(Tos)-methyl ester and Z-Arg(Tos)-amide, as well as of Boc-Arg(Tos)-chloromethyl ketone. The mixed anhydride coupling procedure and the di-Boc-protecting guanidino group induced more delta-lactam formation than any other coupling or NG-protection method. The amide, benzyl, 4-(NO2)-benzyl and methyl alpha-carboxyl-protected amino acids generated more delta-lactam than did those protected by tertbutyl or N2H2-Boc. So far it has not been possible to propose a general mechanism for delta-lactam formation or a process that completely abolishes it. Therefore, this side reaction should be considered almost inevitable.
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