Benzyloxycarbonylarginine (Z-Arg) is a synthetic amino acid derivative commonly used in peptide synthesis. It is an N-protected arginine, where the amino group is protected by a benzyloxycarbonyl (Z) group. This protection strategy allows for selective reactions to occur at other functional groups within the peptide chain. Z-Arg is typically synthesized by reacting arginine with benzyl chloroformate in an alkaline solution. The compound is widely used in solid-phase peptide synthesis (SPPS) as a building block for creating peptides containing arginine residues. Its importance lies in its ability to provide a temporary protection of the amino group, preventing unwanted side reactions and ensuring efficient peptide assembly. Z-Arg is also studied for its potential applications in medicinal chemistry, where it can be used to develop drugs with enhanced stability and bioavailability. The protected arginine residue can be readily removed after peptide synthesis using strong acids or hydrogenolysis, leading to the desired peptide product.'
ID Source | ID |
---|---|
PubMed CID | 71055 |
CHEMBL ID | 1423296 |
SCHEMBL ID | 631840 |
MeSH ID | M0070025 |
Synonym |
---|
AC-17163 |
1234-35-1 |
l-arginine, n2-[(phenylmethoxy)carbonyl]- |
MLS000563719 , |
smr000388882 |
SDCCGMLS-0091585.P001 |
benzyloxycarbonylarginine |
UPCMLD00WJLM29 |
CMLD4_000213 |
z-arg-oh, >=96.0% (nt) |
z-arg-oh |
nalpha-cbz-l-arginine |
nalpha-carbobenzoxy-l-arginine |
(2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid |
A805075 |
(s)-2-(((benzyloxy)carbonyl)amino)-5-((diaminomethylene)ammonio)pentanoate |
NCGC00247325-01 |
M03028 |
cbz-arg-oh |
HMS2214B21 |
z-l-arg-oh |
benzyloxycarbonyl-l-arginine |
einecs 214-973-6 |
n2-((phenylmethoxy)carbonyl)-l-arginine |
l-arginine, n2-((phenylmethoxy)carbonyl)- |
(2s)-5-[bis(azanyl)methylideneamino]-2-(phenylmethoxycarbonylamino)pentanoic acid |
(2s)-2-(benzyloxycarbonylamino)-5-guanidino-valeric acid |
bdbm94463 |
cid_71055 |
AKOS015895268 |
(2s)-2-{[(benzyloxy)carbonyl]amino}-5-carbamimidamidopentanoic acid |
n~2~-[(benzyloxy)carbonyl]-l-arginine |
STL466178 |
SCHEMBL631840 |
(s)-n2-(benzyloxycarbonyl)-arginine |
J-300035 |
cbz-l-arginine |
CHEMBL1423296 |
arginine, n2-[(phenylmethoxy)carbonyl]- |
n-.alpha.-cbz-l-arginine |
n-carbobenzoxy-l-arginine |
arginine, n2-carboxy-, n2-benzyl ester, l- |
n2-benzyloxycarbonyl-l-arginine |
n-2-carbobenzyloxy-l-arginine |
arginine, n-(benzyloxy)carbonyl- |
n-.alpha.-(benzyloxycarbonyl)arginine, l- |
n-alpha-benzyloxycarbonyl-l-arginine (cbz-arg-oh) |
n-alpha-benzyloxycarbonyl-l-arginine |
(2s)-5-(diaminomethylideneammonio)-2-(phenylmethoxycarbonylamino)pentanoate |
R40 , |
(s)-2-(benzyloxycarbonylamino)-5-guanidinopentanoic acid |
AS-12757 |
((benzyloxy)carbonyl)-l-arginine |
D78041 |
DTXSID20883670 |
EN300-302867 |
CS-W012075 |
HY-W011359 |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
lamin isoform A-delta10 | Homo sapiens (human) | Potency | 5.0119 | 0.8913 | 12.0676 | 28.1838 | AID1487 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (20.00) | 29.6817 |
2010's | 3 (60.00) | 24.3611 |
2020's | 1 (20.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.56) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |