Page last updated: 2024-12-06

carbobenzoxyphenylalanine

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Description

Carbobenzoxyphenylalanine (Cbz-Phe) is a derivative of the amino acid phenylalanine, protected at the amino group with a benzyloxycarbonyl (Cbz) group. It is a key intermediate in the synthesis of peptides and proteins, as the Cbz group can be easily removed under mild conditions. Cbz-Phe is commonly used in solid-phase peptide synthesis (SPPS) and other peptide coupling reactions. It is also used as a building block in the synthesis of various biologically active compounds, including pharmaceuticals and agrochemicals. Cbz-Phe has been shown to have some biological activity, including inhibiting the growth of certain cancer cells. Research on Cbz-Phe is driven by its importance as a synthetic intermediate and its potential for biological applications. '

carbobenzoxyphenylalanine: RN given refers to (L-Phe)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID70878
CHEMBL ID66143
SCHEMBL ID220648
MeSH IDM0067569

Synonyms (67)

Synonym
AC-7045
carbobenzoxy-l-phenylalanine
(benzyloxycarbonyl)phenylalanine
n-((phenylmethoxy)carbonyl)-l-phenylalanine
l-n-carboxy-3-phenylalanine n-benzyl ester
n-benzyloxycarbonyl-l-3-phenylalanine
alanine, n-carboxy-3-phenyl-, n-benzyl ester, l-
einecs 214-599-3
l-phenylalanine, n-((phenylmethoxy)carbonyl)-
carbobenzoxyphenylalanine
n-carbobenzoxy-l-phenylalanine
n-benzyloxycarbonyl-s-phenylalanine
cbz-l-phe
(s)-2-benzyloxycarbonylamino-3-phenyl-propionic acid
bdbm50043796
AKOS015839335
cbz-l-phenylalanine
1161-13-3
z-phe-oh, 99%
n-cbz-l-phenylalanine
z-phe-oh
C0660
CHEMBL66143 ,
(2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid
n-(carbobenzyloxy)-l-phenylalanine
n-carbobenzyloxy-l-phenylalanine
cbz-l-phenylalaine
AKOS010373384
(2s)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoic acid
BP-13289
SCHEMBL220648
z-phe
nalpha -benzyloxycarbonyl-l-phenylalanine
n-benzyloxycarbonyl-l-phenyl alanine
benzyloxycarbonyl-l-phenylalanine
z-pheoh
z-(l)-phe-oh
nalpha-benzyloxycarbonyl-l-phenylalanine
n-carbobenzoxy-phenylalanine
n-(benzyloxycarbonyl)-l-phenylalanine
z-l-phe-oh
n-cbz-phenylalanine
n-benzyloxycarbonyl-(l)-phenylalanine
n-cbz phenylalanine
cbz-phe-oh
nalpha -[(phenylmethoxy)carbonyl]-l-phenylalanine
cbz-phe
n-benzyloxycarbonylphenylalanine
zpheoh
benzyloxycarbonylphenylalanine
AM82160
z-l-phenylalanine
n-benzyloxycarbonyl-l-phenylalanine
J-300211
(s)-2-(benzyloxycarbonylamino)-3-phenylpropanoicacid
phenylalanine, n-[(phenylmethoxy)carbonyl]-
CS-W012139
l-phenylalanine, n-[(phenylmethoxy)carbonyl]-
DTXSID30151276
n-alpha-benzyloxycarbonyl-l-phenylalanine
M03068
(s)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanoic acid
D71210
AS-12743
((benzyloxy)carbonyl)-l-phenylalanine
EN300-121295
HY-W011423
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Stromelysin-1Homo sapiens (human)IC50 (µMol)69.50000.00001.148410.0000AID208196; AID208197
Stromelysin-1Homo sapiens (human)Ki58.00000.00030.54258.0000AID208322; AID208323
Substance-P receptorCavia porcellus (domestic guinea pig)IC50 (µMol)40.00000.00002.751810.0000AID208197
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
proteolysisStromelysin-1Homo sapiens (human)
extracellular matrix disassemblyStromelysin-1Homo sapiens (human)
protein catabolic processStromelysin-1Homo sapiens (human)
regulation of cell migrationStromelysin-1Homo sapiens (human)
collagen catabolic processStromelysin-1Homo sapiens (human)
positive regulation of protein-containing complex assemblyStromelysin-1Homo sapiens (human)
cellular response to reactive oxygen speciesStromelysin-1Homo sapiens (human)
innate immune responseStromelysin-1Homo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionStromelysin-1Homo sapiens (human)
cellular response to lipopolysaccharideStromelysin-1Homo sapiens (human)
cellular response to amino acid stimulusStromelysin-1Homo sapiens (human)
cellular response to UV-AStromelysin-1Homo sapiens (human)
cellular response to nitric oxideStromelysin-1Homo sapiens (human)
regulation of neuroinflammatory responseStromelysin-1Homo sapiens (human)
response to amyloid-betaStromelysin-1Homo sapiens (human)
negative regulation of reactive oxygen species metabolic processStromelysin-1Homo sapiens (human)
extracellular matrix organizationStromelysin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
endopeptidase activityStromelysin-1Homo sapiens (human)
metalloendopeptidase activityStromelysin-1Homo sapiens (human)
serine-type endopeptidase activityStromelysin-1Homo sapiens (human)
protein bindingStromelysin-1Homo sapiens (human)
peptidase activityStromelysin-1Homo sapiens (human)
metallopeptidase activityStromelysin-1Homo sapiens (human)
zinc ion bindingStromelysin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionStromelysin-1Homo sapiens (human)
nucleusStromelysin-1Homo sapiens (human)
mitochondrionStromelysin-1Homo sapiens (human)
cytosolStromelysin-1Homo sapiens (human)
extracellular matrixStromelysin-1Homo sapiens (human)
extracellular spaceStromelysin-1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID373680Antibacterial activity against Escherichia coli ATCC 25922 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373676Antibacterial activity against Staphylococcus aureus ATCC 25923 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID208197In vitro inhibition of recombinant stromelysin catalytic domain.1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors.
AID373329Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373677Antibacterial activity against Staphylococcus epidermidis ATCC 12228 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373682Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID1148043Acute toxicity in CF1 mouse1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine.
AID373679Antibacterial activity against Bacillus subtilis ATCC 6633 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373684Antifungal activity against Candida albicans ATCC 10259 after 48 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373681Antibacterial activity against Klebsiella pneumoniae NCIMB 9111 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373325Antibacterial activity against Enterococcus faecalis ATCC 29212 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID208322Inhibition of recombinant full length stromelysin (FLS)1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors.
AID373678Antibacterial activity against Enterococcus faecalis ATCC 29212 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373323Antibacterial activity against Staphylococcus aureus ATCC 25923 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373324Antibacterial activity against Staphylococcus epidermidis ATCC 12228 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373326Antibacterial activity against Bacillus subtilis ATCC 6633 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373683Antifungal activity against Candida albicans ATCC 24433 after 48 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373327Antibacterial activity against Escherichia coli ATCC 25922 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373675Antibacterial activity against Micrococcus luteus ATCC 10240 after 24 hrs by broth microdilution method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373328Antibacterial activity against Klebsiella pneumoniae NCIMB 9111 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID373331Antifungal activity against Candida albicans ATCC 10259 at 20 ug/disk after 72 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID208196Inhibition of recombinant full length stromelysin (FLS).1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors.
AID1148042Antitumor activity against mouse EAC allografted in CF1 mouse assessed as inhibition of tumor growth at 33 mg/kg/day measured on day 71977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine.
AID373322Antibacterial activity against Micrococcus luteus ATCC 10240 at 20 ug/disk after 24 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID208323Inhibition of recombinant stromelysin catalytic domain (SCD)1994Journal of medicinal chemistry, Jan-07, Volume: 37, Issue:1
A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors.
AID373330Antifungal activity against Candida albicans ATCC 24433 at 20 ug/disk after 72 hrs by agar diffusion method2009European journal of medicinal chemistry, Apr, Volume: 44, Issue:4
Synthesis, characterization and antimicrobial activity of Co(II), Zn(II) and Cd(II) complexes with N-benzyloxycarbonyl-S-phenylalanine.
AID1148040Antitumor activity against mouse EAC allografted in CF1 mouse assessed as host survival at 33 mg/kg/day measured on day 71977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine.
AID1148041Antitumor activity against mouse EAC allografted in CF1 mouse assessed as tumor volume at 33 mg/kg/day measured on day 71977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 1. N-Protected vinyl, 1,2-dihaloethyl, and cyanomethyl esters of phenylalanine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (37.50)18.7374
1990's3 (37.50)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.19

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.

MetricThis Compound (vs All)
Research Demand Index12.19 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]