Page last updated: 2024-12-07

glycyl-l-phenylalanine

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

Description

Glycyl-L-phenylalanine (Gly-Phe) is a dipeptide composed of the amino acids glycine and L-phenylalanine. It is a naturally occurring compound found in various proteins.

**Synthesis:** Gly-Phe can be synthesized by various methods, including enzymatic synthesis using peptidases and chemical synthesis using coupling reactions.

**Effects:**

* Gly-Phe exhibits various biological activities. It has been shown to have antioxidant properties, protect against oxidative stress, and possess anti-inflammatory effects.
* Studies suggest potential therapeutic applications in conditions like diabetes, Alzheimer's disease, and cancer.
* It may also play a role in regulating blood pressure and promoting wound healing.

**Importance and Research:**

* Gly-Phe is a valuable model compound for studying peptide structure and function.
* Its biological activities have led to extensive research exploring its potential as a therapeutic agent.
* Research focuses on its synthesis, characterization, and pharmacological effects.
* Studies aim to understand its mechanism of action and optimize its therapeutic potential.

**Other Considerations:**

* Gly-Phe is a constituent of various proteins and peptides, contributing to their overall structure and function.
* It is a valuable building block for synthesizing larger peptides and proteins.
* The availability of Gly-Phe as a reagent has facilitated research in peptide chemistry and biochemistry.'

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

Gly-Phe : A dipeptide formed from glycine and L-phenylalanine residues. [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 CID92953
CHEMBL ID299889
CHEBI ID73912
SCHEMBL ID232699
MeSH IDM0094471

Synonyms (41)

Synonym
nsc-88881
3321-03-7
glycyl-l-phenylalanine
gly-phe
glycyl-phenylalanine
784F522A-C4BB-4849-AC2F-13E036818073
bdbm50188491
(s)-2-(2-amino-acetylamino)-3-phenyl-propionic acid
(glycyldehydrophenylalanine)2-(2-amino-acetylamino)-3-phenyl-propionic acid
2-(2-amino-acetylamino)-3-phenyl-propionic acid
chebi:73912 ,
CHEMBL299889 ,
glycylphenylalanine
G0136
h-gly-phe-oh
(2s)-2-[(2-aminoacetyl)amino]-3-phenylpropanoic acid
n-glycyl-3-phenylalanine
unii-7u35x863xk
nsc 88881
7u35x863xk ,
einecs 222-027-9
AKOS010366203
(s)-2-(2-aminoacetamido)-3-phenylpropanoic acid
AKOS015855060
(2s)-2-(2-aminoacetamido)-3-phenylpropanoic acid
SCHEMBL232699
ds-4524 ,
gly-phe, puriss., >=99.0% (nt)
mfcd00065110
(s)-2-(2-aminoacetamido)-3-phenylpropanoicacid
Q27144236
JBCLFWXMTIKCCB-VIFPVBQESA-N
T72314
alanine, n-glycyl-3-phenyl-, l-
(2s)-2-((2-azaniumylacetyl)amino)-3-phenylpropanoate
n-glycylphenylalanine
l-phenylalanine, glycyl-
n-glycyl-l-phenylalanine
CS-W014714
HY-W013998
DTXSID501344793
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role 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]

Drug Classes (2)

ClassDescription
dipeptideAny molecule that contains two amino-acid residues connected by peptide linkages.
dipeptide zwitterionAny peptide zwitterion comprising two amino acid residues. Major structure at pH 7.3.
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Angiotensin-converting enzyme Homo sapiens (human)IC50 (µMol)616.75850.00010.533610.0000AID38876; AID39018
Solute carrier family 15 member 1Homo sapiens (human)IC50 (µMol)170.00000.18000.19000.2000AID266249
Mu-type opioid receptorCavia porcellus (domestic guinea pig)IC50 (µMol)170.00000.00020.660310.0000AID266249
Solute carrier family 15 member 2Rattus norvegicus (Norway rat)Ki8.00003.00006.47788.5000AID681124
Tripeptidyl-peptidase 2Rattus norvegicus (Norway rat)Ki470.00000.00700.50351.0000AID214629
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation 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]

Biological Processes (62)

Processvia Protein(s)Taxonomy
response to hypoxiaAngiotensin-converting enzyme Homo sapiens (human)
kidney developmentAngiotensin-converting enzyme Homo sapiens (human)
blood vessel remodelingAngiotensin-converting enzyme Homo sapiens (human)
angiotensin maturationAngiotensin-converting enzyme Homo sapiens (human)
regulation of renal output by angiotensinAngiotensin-converting enzyme Homo sapiens (human)
neutrophil mediated immunityAngiotensin-converting enzyme Homo sapiens (human)
antigen processing and presentation of peptide antigen via MHC class IAngiotensin-converting enzyme Homo sapiens (human)
regulation of systemic arterial blood pressure by renin-angiotensinAngiotensin-converting enzyme Homo sapiens (human)
proteolysisAngiotensin-converting enzyme Homo sapiens (human)
spermatogenesisAngiotensin-converting enzyme Homo sapiens (human)
female pregnancyAngiotensin-converting enzyme Homo sapiens (human)
regulation of blood pressureAngiotensin-converting enzyme Homo sapiens (human)
male gonad developmentAngiotensin-converting enzyme Homo sapiens (human)
response to xenobiotic stimulusAngiotensin-converting enzyme Homo sapiens (human)
embryo development ending in birth or egg hatchingAngiotensin-converting enzyme Homo sapiens (human)
post-transcriptional regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gene expressionAngiotensin-converting enzyme Homo sapiens (human)
substance P catabolic processAngiotensin-converting enzyme Homo sapiens (human)
bradykinin catabolic processAngiotensin-converting enzyme Homo sapiens (human)
regulation of smooth muscle cell migrationAngiotensin-converting enzyme Homo sapiens (human)
regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
animal organ regenerationAngiotensin-converting enzyme Homo sapiens (human)
response to nutrient levelsAngiotensin-converting enzyme Homo sapiens (human)
response to lipopolysaccharideAngiotensin-converting enzyme Homo sapiens (human)
mononuclear cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
response to laminar fluid shear stressAngiotensin-converting enzyme Homo sapiens (human)
angiotensin-activated signaling pathwayAngiotensin-converting enzyme Homo sapiens (human)
vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
hormone metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hormone catabolic processAngiotensin-converting enzyme Homo sapiens (human)
eating behaviorAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of apoptotic processAngiotensin-converting enzyme Homo sapiens (human)
peptide catabolic processAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of vasoconstrictionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of glucose importAngiotensin-converting enzyme Homo sapiens (human)
regulation of synaptic plasticityAngiotensin-converting enzyme Homo sapiens (human)
lung alveolus developmentAngiotensin-converting enzyme Homo sapiens (human)
amyloid-beta metabolic processAngiotensin-converting enzyme Homo sapiens (human)
arachidonic acid secretionAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of neurogenesisAngiotensin-converting enzyme Homo sapiens (human)
heart contractionAngiotensin-converting enzyme Homo sapiens (human)
regulation of angiotensin metabolic processAngiotensin-converting enzyme Homo sapiens (human)
hematopoietic stem cell differentiationAngiotensin-converting enzyme Homo sapiens (human)
angiogenesis involved in coronary vascular morphogenesisAngiotensin-converting enzyme Homo sapiens (human)
cellular response to glucose stimulusAngiotensin-converting enzyme Homo sapiens (human)
response to dexamethasoneAngiotensin-converting enzyme Homo sapiens (human)
cell proliferation in bone marrowAngiotensin-converting enzyme Homo sapiens (human)
regulation of heart rate by cardiac conductionAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of calcium ion importAngiotensin-converting enzyme Homo sapiens (human)
response to thyroid hormoneAngiotensin-converting enzyme Homo sapiens (human)
blood vessel diameter maintenanceAngiotensin-converting enzyme Homo sapiens (human)
regulation of hematopoietic stem cell proliferationAngiotensin-converting enzyme Homo sapiens (human)
negative regulation of gap junction assemblyAngiotensin-converting enzyme Homo sapiens (human)
cellular response to aldosteroneAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of peptidyl-cysteine S-nitrosylationAngiotensin-converting enzyme Homo sapiens (human)
positive regulation of systemic arterial blood pressureAngiotensin-converting enzyme Homo sapiens (human)
monoatomic ion transportSolute carrier family 15 member 1Homo sapiens (human)
protein transportSolute carrier family 15 member 1Homo sapiens (human)
peptide transportSolute carrier family 15 member 1Homo sapiens (human)
dipeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
tripeptide import across plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
proton transmembrane transportSolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
endopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
carboxypeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metalloendopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
calmodulin bindingAngiotensin-converting enzyme Homo sapiens (human)
peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
metallopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
exopeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
tripeptidyl-peptidase activityAngiotensin-converting enzyme Homo sapiens (human)
peptidyl-dipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
zinc ion bindingAngiotensin-converting enzyme Homo sapiens (human)
chloride ion bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
bradykinin receptor bindingAngiotensin-converting enzyme Homo sapiens (human)
mitogen-activated protein kinase bindingAngiotensin-converting enzyme Homo sapiens (human)
metallodipeptidase activityAngiotensin-converting enzyme Homo sapiens (human)
heterocyclic compound bindingAngiotensin-converting enzyme Homo sapiens (human)
proton-dependent oligopeptide secondary active transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
peptide:proton symporter activitySolute carrier family 15 member 1Homo sapiens (human)
tripeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
dipeptide transmembrane transporter activitySolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
extracellular regionAngiotensin-converting enzyme Homo sapiens (human)
extracellular spaceAngiotensin-converting enzyme Homo sapiens (human)
lysosomeAngiotensin-converting enzyme Homo sapiens (human)
endosomeAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
external side of plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
basal plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
brush border membraneAngiotensin-converting enzyme Homo sapiens (human)
extracellular exosomeAngiotensin-converting enzyme Homo sapiens (human)
sperm midpieceAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneAngiotensin-converting enzyme Homo sapiens (human)
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
brush borderSolute carrier family 15 member 1Homo sapiens (human)
membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
apical plasma membraneSolute carrier family 15 member 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID19573Stability against mammalian enzyme dehydropeptidase (calculated for 1 microL of enzyme solution and 100 uM substrate).1992Journal of medicinal chemistry, May-15, Volume: 35, Issue:10
Dual-action penems and carbapenems.
AID615024Half life in human plasma2009Bioorganic & medicinal chemistry, May-15, Volume: 17, Issue:10
QSAR models for predicting enzymatic hydrolysis of new chemical entities in 'soft-drug' design.
AID500815Activation of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
AID681125TP_TRANSPORTER: inhibition of Gly-Sar uptake in PEPT1-expressing LLC-PK1 cells2000Pflugers Archiv : European journal of physiology, Sep, Volume: 440, Issue:5
Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2.
AID26797Partition coefficient (logP)1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID39018Inhibitory activity against angiotensin converting enzyme (ACE)1993Journal of medicinal chemistry, Aug-06, Volume: 36, Issue:16
Three-dimensional quantitative structure-activity relationship of angiotesin-converting enzyme and thermolysin inhibitors. II. A comparison of CoMFA models incorporating molecular orbital fields and desolvation free energies based on active-analog and com
AID681124TP_TRANSPORTER: inhibition of Gly-Sar uptake in PEPT2-expressing LLC-PK1 cells2000Pflugers Archiv : European journal of physiology, Sep, Volume: 440, Issue:5
Structural requirements for determining the substrate affinity of peptide transporters PEPT1 and PEPT2.
AID266249Binding affinity to human PEPT1 assessed as inhibition of [14C]Gly-Sar uptake in MDCK cells2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID228722Bitter tasting threshold was expressed as log 1/T.1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Amino acid side chain descriptors for quantitative structure-activity relationship studies of peptide analogues.
AID1183271Inhibition of ACE (unknown origin)2014European journal of medicinal chemistry, Sep-12, Volume: 84CoMFA and CoMSIA analysis of ACE-inhibitory, antimicrobial and bitter-tasting peptides.
AID266247Activation of human PEPT1 expressed in MDCK cells relative to Gly-Sar2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID678988TP_TRANSPORTER: uptake in PEPT2-expressing HeLa cells1998The American journal of physiology, 10, Volume: 275, Issue:4
Electrophysiological characteristics of the proton-coupled peptide transporter PEPT2 cloned from rat brain.
AID266246Activation of human PEPT1 expressed in MDCK cells2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID214629Inhibition potency against Cholecystokinin-8-Inactivating Peptidase (Serine Peptidase).2000Journal of medicinal chemistry, Feb-24, Volume: 43, Issue:4
Inhibitors of tripeptidyl peptidase II. 2. Generation of the first novel lead inhibitor of cholecystokinin-8-inactivating peptidase: a strategy for the design of peptidase inhibitors.
AID38876Biological activity was measured against Angiotensin I converting enzyme1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Amino acid side chain descriptors for quantitative structure-activity relationship studies of peptide analogues.
AID266248Ratio of %GSmax to EC50 for human PEPT1 activation2006Journal of medicinal chemistry, Jun-15, Volume: 49, Issue:12
Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding.
AID233318Bitter threshold value1987Journal of medicinal chemistry, Oct, Volume: 30, Issue:10
Quantitative structure-activity relationships of the bitter thresholds of amino acids, peptides, and their derivatives.
AID500816Inhibition of nitrogen-starved wild type sigma1278b yeast Gap1-mediated amino acid uptake at 5 mM after 60 secs relative to L-citrulline2009Nature chemical biology, Jan, Volume: 5, Issue:1
Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.
AID679557TP_TRANSPORTER: inhibition of Gly-Sar uptake (Gly-Sar: 30 uM, Gly-Phe: 10000 uM) in PEPT2-expressing HeLa cells1995Biochimica et biophysica acta, May-04, Volume: 1235, Issue:2
Molecular cloning of PEPT 2, a new member of the H+/peptide cotransporter family, from human kidney.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (50)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (22.00)18.7374
1990's13 (26.00)18.2507
2000's15 (30.00)29.6817
2010's10 (20.00)24.3611
2020's1 (2.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.57

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 Index22.57 (24.57)
Research Supply Index3.97 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.92%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other51 (98.08%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]