Compounds > tert-butyloxycarbonyltryptophan
Page last updated: 2024-11-06

tert-butyloxycarbonyltryptophan

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Description

tert-Butyloxycarbonyltryptophan (Boc-Trp) is a protected amino acid derivative commonly used in peptide synthesis. It is synthesized by reacting tryptophan with di-tert-butyl dicarbonate (Boc2O) under basic conditions. The tert-butyloxycarbonyl (Boc) group serves as a protecting group for the amino group of tryptophan, preventing unwanted side reactions during peptide synthesis. Boc-Trp is a valuable reagent for the preparation of peptides, as it allows for the controlled introduction of tryptophan residues into peptide chains. The Boc group can be selectively removed under acidic conditions, allowing for the subsequent coupling of other amino acids to the free amino group of tryptophan. Boc-Trp is also used in the synthesis of various biologically active peptides, including neuropeptides, hormones, and enzymes. Its importance in research lies in its ability to facilitate the efficient and controlled synthesis of complex peptides. The study of Boc-Trp is crucial for understanding peptide synthesis, peptide structure-activity relationships, and the development of novel peptides with therapeutic potential.'

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

Cross-References

ID SourceID
PubMed CID83169
CHEMBL ID65709
CHEBI ID183830
SCHEMBL ID1003555
MeSH IDM0132403

Synonyms (72)

Synonym
AC-17135
bdbm50043801
(s)-2-tert-butoxycarbonylamino-3-(1h-indol-3-yl)-propionic acid
tert-butoxycarbonyltryptophan
tert-butoxycarbonyl-l-tryptophan
n-tert-butoxycarbonyl-l-(-)-tryptophan
n-tert-butoxycarbonyltryptophan
13139-14-5
tert-butyloxycarbonyltryptophan
n-tert-butyloxycarbonyl-l-tryptophan
n-tert-butoxycarbonyl-l-tryptophan
NCGC00166098-01
n-(tert-butoxycarbonyl)-l-tryptophan
n-boc-l-tryptophan
boc-trp-oh
B1639
CHEMBL65709 ,
CHEBI:183830
n-[(tert-butoxy)carbonyl]-l-tryptophan
(2s)-3-(1h-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
EN300-52850
(2s)-2-{[(tert-butoxy)carbonyl]amino}-3-(1h-indol-3-yl)propanoic acid
l-tryptophan, n-((1,1-dimethylethoxy)carbonyl)-
n-((tert-butoxy)carbonyl)-l-tryptophan
nsc 334306
n-((1,1-dimethylethoxy)carbonyl)-l-tryptophan
tryptophan, n-carboxy-, n-tert-butyl ester, l-
einecs 236-072-7
AKOS015922872
boc-l-trp-oh
AKOS005175158
AM20060456
l-tryptophan, n-[(1,1-dimethylethoxy)carbonyl]-
nalpha -t-butoxycarbonyl-l-tryptophan
tert-butyloxycarbonyl-l-tryptophan
NFVNYBJCJGKVQK-ZDUSSCGKSA-N
nalpha-tert-butoxycarbonyl-l-tryptophan
boctrpoh
boc-l-tryptophan
n-t-butoxycarbonyltryptophan
boc-trytophan
nalpha-t-butoxycarbonyl-l-tryptophan
nalpha -t-butoxycarbonyl-l-tryptophane
n-t-butoxycarbonyl-l-tryptophan
n-tert.butoxycarbonyl-tryptophan
boc-l-tryptophane
t-butoxycarbonyltryptophan
n-(t-butoxycarbonyl)tryptophan
SCHEMBL1003555
J-300267
(s)-2-((tert-butoxycarbonyl)amino)-3-(1h-indol-3-yl)propanoic acid
Q-101608
(tert-butoxycarbonyl)-l-tryptophan
mfcd00065595
n-alpha-t-butyloxycarbonyl-l-tryptophane
SR-01000388673-1
sr-01000388673
na-(tert-butoxycarbonyl)-l-tryptophan
na-boc-l-tryptophan
M03328
boc-trp-oh, >=99.0% (tlc)
CS-D1147
nalpha-boc-l-tryptophan
(s)-2-(tert-butoxycarbonylamino)-3-(1h-indol-3-yl)propanoic acid
AS-12736
AC7874
n-boc-tryptophan
DTXSID20884506
A847884
nalpha-(tert-butoxycarbonyl)-l-tryptophan, boc-l-trp-oh
nalpha-boc-l-tryptophane;boc-trp-oh
Z756448322
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
indolyl carboxylic acid
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DNA polymerase kappa isoform 1Homo sapiens (human)Potency15.00300.031622.3146100.0000AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Stromelysin-1Homo sapiens (human)IC50 (µMol)10.00000.00001.148410.0000AID208197
Stromelysin-1Homo sapiens (human)Ki8.00000.00030.54258.0000AID208323
Substance-P receptorCavia porcellus (domestic guinea pig)IC50 (µMol)10.00000.00002.751810.0000AID208197
[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 (13)

Assay IDTitleYearJournalArticle
AID568388Antimicrobial activity against Xanthomonas oryzae after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID568390Antimicrobial activity against coagulase positive Staphylococcus after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
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.
AID568393Antifungal activity against Fusarium oxysporum after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID568389Antimicrobial activity against Klebsiella pneumoniae after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID1226027Retention time of the compound by HPLC analysis2015ACS medicinal chemistry letters, Mar-12, Volume: 6, Issue:3
N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.
AID568392Antifungal activity against Aspergillus flavus after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID568387Antimicrobial activity against Escherichia coli after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID1226026Activity of 0.1 uM recombinant human IDO assessed as compound consumption at 100 uM after 1 hr by fluorescence detection method relative to control2015ACS medicinal chemistry letters, Mar-12, Volume: 6, Issue:3
N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.
AID568391Antifungal activity against Aspergillus niger after 72 hrs by microdilution method2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Synthesis of elastin based peptides conjugated to benzisoxazole as a new class of potent antimicrobials--A novel approach to enhance biocompatibility.
AID1226025Activity of 0.5 uM recombinant human IDO assessed as compound consumption at 100 uM after 1 hr by fluorescence detection method relative to control2015ACS medicinal chemistry letters, Mar-12, Volume: 6, Issue:3
N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.
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.
AID1226024Activity of 5 uM recombinant human IDO assessed as compound consumption at 1000 uM after 4 hrs by UV detection method relative to control2015ACS medicinal chemistry letters, Mar-12, Volume: 6, Issue:3
N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's3 (42.86)18.2507
2000's0 (0.00)29.6817
2010's3 (42.86)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: 12.59

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 Index12.59 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.59)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
kynurenine
Kynurenine: A metabolite of the essential amino acid tryptophan metabolized via the tryptophan-kynurenine pathway.. kynurenine : A ketone that is alanine in which one of the methyl hydrogens is substituted by a 2-aminobenzoyl group.		1.9910aromatic ketone;
non-proteinogenic alpha-amino acid;
substituted aniline		human metabolite
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		1.9910monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
tryptamine
[no description available]		2.1110aminoalkylindole;
aralkylamino compound;
indole alkaloid;
tryptamines		human metabolite;
mouse metabolite;
plant metabolite
phenylalanine
Phenylalanine: An essential aromatic amino acid that is a precursor of MELANIN; DOPAMINE; noradrenalin (NOREPINEPHRINE), and THYROXINE.. L-phenylalanine : The L-enantiomer of phenylalanine.. phenylalanine : An aromatic amino acid that is alanine in which one of the methyl hydrogens is substituted by a phenyl group.		1.9610amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
phenylalanine;
proteinogenic amino acid		algal metabolite;
EC 3.1.3.1 (alkaline phosphatase) inhibitor;
Escherichia coli metabolite;
human xenobiotic metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
tryptophan
Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.		3.2560erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid zwitterion;
L-alpha-amino acid;
proteinogenic amino acid;
tryptophan zwitterion;
tryptophan		antidepressant;
Escherichia coli metabolite;
human metabolite;
micronutrient;
mouse metabolite;
nutraceutical;
plant metabolite;
Saccharomyces cerevisiae metabolite
D-tryptophan
[no description available]		1.9810D-alpha-amino acid;
tryptophan zwitterion;
tryptophan		bacterial metabolite
indopan
indopan: RN given refers to parent cpd without isomeric designation. alpha-methyltryptamine : A tryptamine derivative having a methyl substituent at the alpha-position.		2.1110tryptamines
carbendazim
carbendazim: carcinogen when combined with sodium nitrite; principle metabolite of thiophanate methyl & benomyl; structure. carbendazim : A member of the class of benzimidazoles that is 2-aminobenzimidazole in which the primary amino group is substituted by a methoxycarbonyl group. A fungicide, carbendazim controls Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops, including bananas, cereals, cotton, fruits, grapes, mushrooms, ornamentals, peanuts, sugarbeet, soybeans, tobacco, and vegetables.		2.0610benzimidazole fungicide;
benzimidazoles;
benzimidazolylcarbamate fungicide;
carbamate ester		antifungal agrochemical;
antinematodal drug;
metabolite;
microtubule-destabilising agent
amoxicillin
Amoxicillin: A broad-spectrum semisynthetic antibiotic similar to AMPICILLIN except that its resistance to gastric acid permits higher serum levels with oral administration.. amoxicillin : A penicillin in which the substituent at position 6 of the penam ring is a 2-amino-2-(4-hydroxyphenyl)acetamido group.		2.0610penicillin allergen;
penicillin		antibacterial drug
peroxynitric acid
[no description available]		1.9910nitrogen oxoacid
n-acetyltyrosine
N-acetyl-L-tyrosine : An N-acetyltyrosine in which the chiral centre has L configuration.		1.9810N-acetyltyrosine;
N-acyl-L-tyrosine		biomarker;
EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor;
human urinary metabolite
carbobenzoxyphenylalanine
carbobenzoxyphenylalanine: RN given refers to (L-Phe)-isomer		1.9810
benzyloxycarbonyltryptophan
benzyloxycarbonyltryptophan: receptor antagonist for peptides from gastrin family; RN given refers to (L)-isomer		2.3820
kynurenine
L-kynurenine : A kynurenine that has L configuration.		2.1110amino acid zwitterion;
kynurenine;
non-proteinogenic L-alpha-amino acid		human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
5-hydroxytryptophan
hydroxytryptophan : A hydroxy-amino acid that is tryptophan substituted by at least one hydroxy group at unspecified position.. 5-hydroxy-L-tryptophan : The L-enantiomer of 5-hydroxytryptophan.		2.11105-hydroxytryptophan;
amino acid zwitterion;
hydroxy-L-tryptophan;
non-proteinogenic L-alpha-amino acid		human metabolite;
mouse metabolite;
plant metabolite
n'-formylkynurenine
N'-formylkynurenine: a photochemical breakdown product of tryptophan in proteins; RN given refers to parent cpd without isomeric designation		2.4320amino acid zwitterion;
N-formylkynurenine;
non-proteinogenic amino acid derivative;
non-proteinogenic L-alpha-amino acid		human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
n-acetyl-d-tryptophan
[no description available]		1.9810D-tryptophan derivative;
N-acetyl-D-amino acid
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		1.9910cyclodextrin
1-methyltryptophan
1-methyltryptophan: an immunomodulator. 1-methyltryptophan : A tryptophan derivative that is tryptophan carrying a single methyl substituent at position 1 on the indole.		2.1110indolyl carboxylic acid
n-acetyltryptophan
N-acetyl-L-tryptophan : A N-acetyl-L-amino acid that is the N-acetyl derivative of L-tryptophan.		2.4220L-tryptophan derivative;
N-acetyl-L-amino acid		metabolite
benzotript
benzotript: anti-gastrinic; active group is amide; structure		1.9610
gastrins
Gastrins: A family of gastrointestinal peptide hormones that excite the secretion of GASTRIC JUICE. They may also occur in the central nervous system where they are presumed to be neurotransmitters.		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials