Nα-Z-Nω,Nω'-(di-tert-butyloxycarbonyl)-L-arginine cyclohexylammonium salt
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Nα-Z-Nω,Nω'-(di-tert-butyloxycarbonyl)-L-arginine cyclohexylammonium salt

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Category
CBZ-Amino Acids
Catalog number
BAT-003257
CAS number
145315-39-5
Molecular Formula
C24H36N4O8·C6H13N
Molecular Weight
607.75
Nα-Z-Nω,Nω'-(di-tert-butyloxycarbonyl)-L-arginine cyclohexylammonium salt
IUPAC Name
(2S)-5-[[amino-[bis[(2-methylpropan-2-yl)oxycarbonyl]amino]methylidene]amino]-2-(phenylmethoxycarbonylamino)pentanoic acid;cyclohexanamine
Synonyms
Z-L-Arg(Boc)2-OH CHA
Appearance
White powder
Purity
≥ 98% (NMR)
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H36N4O8.C6H13N/c1-23(2,3)35-21(32)28(22(33)36-24(4,5)6)19(25)26-14-10-13-17(18(29)30)27-20(31)34-15-16-11-8-7-9-12-16;7-6-4-2-1-3-5-6/h7-9,11-12,17H,10,13-15H2,1-6H3,(H2,25,26)(H,27,31)(H,29,30);6H,1-5,7H2/t17-;/m0./s1
InChI Key
QBGRVFFDXXNSRE-LMOVPXPDSA-N
Canonical SMILES
CC(C)(C)OC(=O)N(C(=NCCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1)N)C(=O)OC(C)(C)C.C1CCC(CC1)N

Nα-Z-Nω,Nω'-(di-tert-butyloxycarbonyl)-L-arginine cyclohexylammonium salt, a derivative of the amino acid arginine, finds diverse applications in biochemical and pharmaceutical realms. Delve into its key applications presented with heightened perplexity and burstiness:

Peptide Synthesis: A cornerstone in peptide chemistry, this compound serves as a critical protecting group, shielding reactive sites like the guanidine functionality of arginine. This selective masking allows chemists to meticulously construct intricate peptide chains free from undesired reactions. The protective veil can later be delicately lifted, yielding pure peptides with unparalleled precision.

Drug Development: At the forefront of pharmaceutical innovation, Nα-Z-Nω,Nω'-(di-tert-butyloxycarbonyl)-L-arginine cyclohexylammonium salt plays a pivotal role in synthesizing arginine-based therapeutic molecules. Its use ensures the safeguarding of arginine's reactive side chains throughout complex chemical transformations, guaranteeing structural integrity crucial for developing efficacious drugs.

Enzyme Inhibition Studies: Unraveling enzyme intricacies, this compound emerges as a valuable tool in probing enzyme mechanisms, especially those entwined with arginine residues. By offering a shielded arginine analogue, researchers can explore the impact of altering the arginine side chain on enzyme behavior and specificity, pivotal for designing enzyme inhibitors with potential therapeutic benefits.

Structural Biology: In the realm of structural biology, this compound finds its place in crystallizing proteins housing arginine residues. Through safeguarding these key residues, researchers navigate away from unwanted interactions during protein crystal formation, enabling the acquisition of high-resolution protein complex structures. This elucidates protein functionality and interactions, enriching our comprehension of biological intricacies.

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