Page last updated: 2024-12-05

n-benzyloxycarbonylglycine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

n-Benzyloxycarbonylglycine, also known as Z-glycine, is a protected amino acid derivative commonly used in peptide synthesis. It is synthesized through a reaction between glycine and benzyl chloroformate in the presence of a base. The benzyloxycarbonyl (Z) group acts as a protecting group for the amino group of glycine, preventing unwanted side reactions during peptide coupling. Z-glycine is particularly important in peptide synthesis because it allows for the selective activation and coupling of the carboxyl group, enabling the stepwise assembly of complex peptide chains. The Z group can be easily removed under mild conditions, such as catalytic hydrogenation, to reveal the free amino group for further peptide synthesis. The study of Z-glycine and its use in peptide synthesis is essential for understanding and developing new methods for the synthesis of biologically active peptides and proteins. These peptides are used in various fields, including medicine, biotechnology, and materials science.'

N-benzyloxycarbonylglycine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

N-benzyloxycarbonylglycine : A derivative of glycine having a benzyloxycarbonyl protecting group attached to the nitrogen. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

FloraRankFlora DefinitionFamilyFamily Definition
GlycinegenusA non-essential amino acid. It is found primarily in gelatin and silk fibroin and used therapeutically as a nutrient. It is also a fast inhibitory neurotransmitter.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID14349
CHEMBL ID101287
CHEBI ID16532
SCHEMBL ID126974
MeSH IDM0233061

Synonyms (102)

Synonym
AC-17144
2-phenylmethoxycarbonylamino-acetic acid
carbobenzoxyglycine
glycine, n-benzyl ester
carbobenzyloxyglycine
glycine, n-[(phenylmethoxy)carbonyl]-
(cbz)gly
z-gly
benzyloxycarbonylglycine
nsc-2526
n-carboxyglycine n-benzyl ester
n-carbobenzoxyglycine
nsc2526
n-carbobenzyloxyglycine
CHEBI:16532 ,
carbobenzoxyl glycine
n-(benzyloxycarbonyl)glycine
z-gly-oh
OPREA1_763666
brn 0526877
einecs 214-516-0
n-((phenylmethoxy)carbonyl)glycine
glycine, n-carboxy-, n-benzyl ester
glycine, n-((phenylmethoxy)carbonyl)-
nsc 2526
OPREA1_774492
inchi=1/c10h11no4/c12-9(13)6-11-10(14)15-7-8-4-2-1-3-5-8/h1-5h,6-7h2,(h,11,14)(h,12,13
glycine,n-benzyloxycarbonyl
n-[(benzyloxy)carbonyl]glycine
n-cbz-glycine
C03710
n-benzyloxycarbonylglycine
1138-80-3
benzyloxycarbonylamino-acetic acid anion
z-gly-oh, 99%
AKOS000163682
2-(phenylmethoxycarbonylamino)acetic acid
n-carbobenzoxy-glycine
CHEMBL101287
benzyloxycarbonylamino-acetic acid
A803102
((benzyloxy)carbonyl)glycinate
2-{[(benzyloxy)carbonyl]amino}acetic acid
cbz-gly-oh
cbz-gly
4-06-00-02286 (beilstein handbook reference)
cbz-glycine
FT-0633395
AB00257
n-alpha-cbz-glycine
benzyloxycarbonyl-glycine
cbz glycine
[(benzyloxy)-carbonyl]aminoacetic acid
((benzyloxy)carbonyl)glycine
2-(((benzyloxy)carbonyl)amino)acetic acid
n-cbz-gly-oh
2-(benzyloxycabonylamino)acetic acid
benzyloxycarbonyl glycine
n-z-gly-oh
carbobenzoxy-glycine
carbobenzoxy-glycin
n-(phenylmethoxycarbonyl)glycine
n-(carbobenzoxy)-glycine
n-[(phenylmethoxy)carbonyl]glycine
n-carbobenzyloxy-glycine
n-cbz glycine
n-benzyloxycarbonyl-glycine
n-(benzyloxycarbonyl) glycine
(benzyloxycarbonyl)-glycine
benzyloxycarbonylaminoacetic acid
n-{[(phenylmethyl)oxy]carbonyl}glycine
2-(benzyloxycarbonylamino)acetic acid
n-(benzyloxycarbonyl)-glycine
n-benzyloxycarbonyl glycine
n-benzyloxycarbonyl-glycin
z-glyoh
2-benzyloxycarbonylaminoacetic acid
SCHEMBL126974
z-glycine
AM81784
2P-917
DTXSID8061559
Q-101746
([(benzyloxy)carbonyl]amino)acetic acid #
(carbobenzyloxy)glycine
n-(carbobenzoxy)glycine
mfcd00002691
2-(phenylmethoxycarbonylamino)ethanoic acid
F2191-0118
M03051
bdbm223537
us9321743, cbz-gly
SY006638
CS-W018534
n-[(phenylmethoxy)carbonyl]-glycine
methyl 5-cyano-2,2-diphenylpentanoate
Q27101958
EN300-53412
2-(((benzyloxy)carbonyl)amino)aceticacid
HY-Y0967
glycine-13c2-15n, n-[(phenylmethoxy)carbonyl]-
Z285919546
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylglycineAn N-acyl-amino acid in which amino acid specified is glycine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID110573The average latency on the onset of the seizures compared to the controls after 3 hr in the strychnine test in mice at a dose of 418 mg/kg, ip; Not determined1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID388274Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase relative to hippuric acid2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID110572The average latency on the onset of the seizures compared to the controls after 3 hr in the strychnine test in mice at a dose of 209 mg/kg1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID155411Papain-catalyzed hydrolysis was expressed as Km1984Journal of medicinal chemistry, Jun, Volume: 27, Issue:6
Vinylogous amino acid esters: a new class of inactivators for thiol proteases.
AID110564The average latency on the onset of the seizures compared to the controls after 30 min in the strychnine test in mice at a dose of 209 mg/kg1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID120089Percent of the tonic seizures after 30 min in the 3-mercaptopropionic acid test in mice at a dose of 418 mg/kg, ip1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID120088Percent of the tonic seizures after 30 min in the 3-mercaptopropionic acid test in mice at a dose of 209 mg/kg, ip1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID120093Percent of the tonic seizures after 3h in the 3-mercaptopropionic acid test in mice at a dose of 209 mg/kg, ip1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID1148054Antineoplastic activity against mouse EAC allografted in CF1 mouse assessed as tumor growth inhibition on day 7 measured at 33 mg/kg1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 2. Structure-activity studies on N-protected vinyl, 1,2-dibromoethyl, and cyanomethyl esters of several amino acids.
AID118596Compound was tested for anticonvulsant activity in maximal electroshock seizure(MES) test after 30 min upon intraperitoneal administration to mice at a dose of 84 mg/kg; Animals protected / Animals tested = 2/81998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID1148053Antineoplastic activity against mouse EAC allografted in CF1 mouse assessed as ascites volume on day 7 measured at 33 mg/kg (Rvb = 4.1 +/- 1.24 mL)1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 2. Structure-activity studies on N-protected vinyl, 1,2-dibromoethyl, and cyanomethyl esters of several amino acids.
AID388272Activity of rat recombinant peptidylglycine alpha-amidating monooxygenase assessed as stimulation of oxygen consumption2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID1148052Antineoplastic activity against mouse EAC allografted in CF1 mouse assessed as packed cell volume on day 7 measured at 33 mg/kg (Rvb = 32.75 +/- 7.87%)1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Antineoplastic agents. 2. Structure-activity studies on N-protected vinyl, 1,2-dibromoethyl, and cyanomethyl esters of several amino acids.
AID120094Percent of the tonic seizures after 3h in the 3-mercaptopropionic acid test in mice at a dose of 418mg/kg, ip1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID388273Ratio of Vm(app) to Km(app) for rat recombinant peptidylglycine alpha-amidating monooxygenase2008Bioorganic & medicinal chemistry, Dec-01, Volume: 16, Issue:23
Substituted hippurates and hippurate analogs as substrates and inhibitors of peptidylglycine alpha-hydroxylating monooxygenase (PHM).
AID110566The average latency on the onset of the seizures compared to the controls after 30 min in the strychnine test in mice at a dose of 418 mg/kg, ip; Not determined1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
AID112305Compound was tested for anticonvulsant activity in maximal electroshock seizure(MES) test after 3 hours upon intraperitoneal administration to mice1998Journal of medicinal chemistry, Jan-01, Volume: 41, Issue:1
N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants.
[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-19902 (25.00)18.7374
1990's3 (37.50)18.2507
2000's2 (25.00)29.6817
2010's0 (0.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.39

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.39 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.40 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.39)

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]