Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:17 UTC
Update Date2022-09-22 18:34:22 UTC
HMDB IDHMDB0028995
Secondary Accession Numbers
  • HMDB28995
Metabolite Identification
Common NamePhenylalanylglycine
DescriptionPhenylalanylglycine is a dipeptide composed of phenylalanine and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1582753364
Synonyms
ValueSource
F-GChEBI
FGChEBI
L-Phe-glyChEBI
F-g DipeptideHMDB
FG DipeptideHMDB
L-PhenylalanylglycineHMDB
N-L-PhenylalanylglycineHMDB
N-PhenylalanylglycineHMDB
Phe-glyHMDB
Phenylalanine glycine dipeptideHMDB
Phenylalanine-glycine dipeptideHMDB
Phenylalanyl-glycineHMDB
PhenylalanylglycineChEBI
Chemical FormulaC11H14N2O3
Average Molecular Weight222.244
Monoisotopic Molecular Weight222.100442319
IUPAC Name2-[(2S)-2-amino-3-phenylpropanamido]acetic acid
Traditional Name[(2S)-2-amino-3-phenylpropanamido]acetic acid
CAS Registry Number721-90-4
SMILES
N[C@@H](CC1=CC=CC=C1)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C11H14N2O3/c12-9(11(16)13-7-10(14)15)6-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1
InChI KeyGLUBLISJVJFHQS-VIFPVBQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty amide
  • Fatty acyl
  • Benzenoid
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid salt
  • Amino acid
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic salt
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.29Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.78 g/LALOGPS
logP-0.9ALOGPS
logP-2.3ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)8.01ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity57.92 m³·mol⁻¹ChemAxon
Polarizability22.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+150.04330932474
DeepCCS[M-H]-147.64830932474
DeepCCS[M-2H]-180.76330932474
DeepCCS[M+Na]+155.95630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhenylalanylglycineN[C@@H](CC1=CC=CC=C1)C(=O)NCC(O)=O3388.8Standard polar33892256
PhenylalanylglycineN[C@@H](CC1=CC=CC=C1)C(=O)NCC(O)=O1674.2Standard non polar33892256
PhenylalanylglycineN[C@@H](CC1=CC=CC=C1)C(=O)NCC(O)=O2241.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phenylalanylglycine,1TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)[C@@H](N)CC1=CC=CC=C12135.5Semi standard non polar33892256
Phenylalanylglycine,1TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O2164.8Semi standard non polar33892256
Phenylalanylglycine,1TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@@H](N)CC1=CC=CC=C12105.3Semi standard non polar33892256
Phenylalanylglycine,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O[Si](C)(C)C2151.3Semi standard non polar33892256
Phenylalanylglycine,2TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O[Si](C)(C)C2131.0Standard non polar33892256
Phenylalanylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2074.4Semi standard non polar33892256
Phenylalanylglycine,2TMS,isomer #2C[Si](C)(C)OC(=O)CN(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C2148.1Standard non polar33892256
Phenylalanylglycine,2TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O)[Si](C)(C)C2310.7Semi standard non polar33892256
Phenylalanylglycine,2TMS,isomer #3C[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O)[Si](C)(C)C2158.4Standard non polar33892256
Phenylalanylglycine,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C2161.3Semi standard non polar33892256
Phenylalanylglycine,2TMS,isomer #4C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C2166.8Standard non polar33892256
Phenylalanylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2269.2Semi standard non polar33892256
Phenylalanylglycine,3TMS,isomer #1C[Si](C)(C)OC(=O)CNC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2241.6Standard non polar33892256
Phenylalanylglycine,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C2111.1Semi standard non polar33892256
Phenylalanylglycine,3TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C2212.2Standard non polar33892256
Phenylalanylglycine,3TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2267.2Semi standard non polar33892256
Phenylalanylglycine,3TMS,isomer #3C[Si](C)(C)N(CC(=O)O)C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C2293.2Standard non polar33892256
Phenylalanylglycine,4TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2295.4Semi standard non polar33892256
Phenylalanylglycine,4TMS,isomer #1C[Si](C)(C)OC(=O)CN(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C2334.5Standard non polar33892256
Phenylalanylglycine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@@H](N)CC1=CC=CC=C12389.7Semi standard non polar33892256
Phenylalanylglycine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O2385.9Semi standard non polar33892256
Phenylalanylglycine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@@H](N)CC1=CC=CC=C12348.2Semi standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2609.8Semi standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2527.8Standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2587.6Semi standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@@H](N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2554.3Standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C2754.3Semi standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC=CC=C1)C(=O)NCC(=O)O)[Si](C)(C)C(C)(C)C2546.8Standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2621.4Semi standard non polar33892256
Phenylalanylglycine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2558.9Standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2967.0Semi standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2798.3Standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2815.5Semi standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC=CC=C1)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2780.8Standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2957.8Semi standard non polar33892256
Phenylalanylglycine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2835.2Standard non polar33892256
Phenylalanylglycine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3153.8Semi standard non polar33892256
Phenylalanylglycine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)[C@H](CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3049.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phenylalanylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phenylalanylglycine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 10V, Positive-QTOFsplash10-00di-1910000000-69f6b703e4914169a9602021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 20V, Positive-QTOFsplash10-006x-9400000000-d2f0749424189385b61c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 40V, Positive-QTOFsplash10-0006-9500000000-990725f616a8528390882021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 10V, Negative-QTOFsplash10-00di-1190000000-d9cf02536a5a863769b32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 20V, Negative-QTOFsplash10-0006-9810000000-3c953bf79faee88c837e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phenylalanylglycine 40V, Negative-QTOFsplash10-05bf-9200000000-a42bc5f9b3b0a4113bf42021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112015
KNApSAcK IDNot Available
Chemspider ID5360444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6992303
PDB IDNot Available
ChEBI ID73635
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pingitore F, Wesdemiotis C: Characterization of dipeptide isomers by tandem mass spectrometry of their mono- versus dilithiated complexes. Anal Chem. 2005 Mar 15;77(6):1796-806. [PubMed:15762588 ]
  2. Thirumoorthy K, Soni K, Nandi N: The molecular recognition of dipeptide by oligoglycyl head group of amphiphile: a quantum chemical study. J Nanosci Nanotechnol. 2009 Jan;9(1):77-89. [PubMed:19441281 ]
  3. Epand RM: Virus replication inhibitory peptide inhibits the conversion of phospholipid bilayers to the hexagonal phase. Biosci Rep. 1986 Jul;6(7):647-53. [PubMed:3779040 ]
  4. Storer AC, Angus RH, Carey PR: Comparison of the kinetics of the papain-catalyzed hydrolysis of glycine- and alanine-based esters and thiono esters. Biochemistry. 1988 Jan 12;27(1):264-8. [PubMed:3349032 ]
  5. Li L, Zheng LX, Yang FY: Effect of propensity of hexagonal II phase formation on the activity of mitochondrial ubiquinol-cytochrome c reductase and H(+)-ATPase. Chem Phys Lipids. 1995 Jun 19;76(2):135-44. [PubMed:7634362 ]
  6. Ningsih F, Kitani S, Fukushima E, Nihira T: VisG is essential for biosynthesis of virginiamycin S, a streptogramin type B antibiotic, as a provider of the nonproteinogenic amino acid phenylglycine. Microbiology. 2011 Nov;157(Pt 11):3213-20. doi: 10.1099/mic.0.050203-0. Epub 2011 Aug 4. [PubMed:21816878 ]
  7. Kruger RG, Lu W, Oberthur M, Tao J, Kahne D, Walsh CT: Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operons. Chem Biol. 2005 Jan;12(1):131-40. [PubMed:15664522 ]
  8. Makowski M, Lisowski M, Maciag A, Wiktor M, Szlachcic A, Lis T: Two pentadehydropeptides with different configurations of the DeltaPhe residues. Acta Crystallogr C. 2010 Mar;66(Pt 3):o119-23. doi: 10.1107/S0108270110003094. Epub 2010 Feb 3. [PubMed:20203407 ]
  9. Fujita T, Morishita Y, Ito H, Kuribayashi D, Yamamoto A, Muranishi S: Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids. Life Sci. 1997;61(25):2455-65. [PubMed:9416764 ]
  10. Yeagle PL, Young J, Hui SW, Epand RM: On the mechanism of inhibition of viral and vesicle membrane fusion by carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine. Biochemistry. 1992 Mar 31;31(12):3177-83. [PubMed:1554703 ]
  11. Varela AS, Bosco Lopez Saez JJ: Utility of serum activity of angiotensin-converting enzyme as a tumor marker. Oncology. 1993 Nov-Dec;50(6):430-5. [PubMed:8233282 ]
  12. Wang P, Polce MJ, Ohanessian G, Wesdemiotis C: The sodium ion affinities of cytosine and its methylated derivatives. J Mass Spectrom. 2008 Apr;43(4):485-94. [PubMed:17994645 ]
  13. Andersson LI, Muller R, Vlatakis G, Mosbach K: Mimics of the binding sites of opioid receptors obtained by molecular imprinting of enkephalin and morphine. Proc Natl Acad Sci U S A. 1995 May 23;92(11):4788-92. [PubMed:7761401 ]
  14. Mizuma T, Masubuchi S, Awazu S: Intestinal absorption of stable cyclic glycylphenylalanine: comparison with the linear form. J Pharm Pharmacol. 1997 Nov;49(11):1067-71. [PubMed:9401939 ]
  15. Ram S, Buchsbaum DJ: Synthesis of a new class of isothiocyanatopeptide bifunctional chelating agents for coupling to monoclonal antibodies. Int J Pept Protein Res. 1996 Jul;48(1):79-86. [PubMed:8844266 ]
  16. Yeagle PL, Dentino AR, Smith FT, Spooner P, Watts A: The antiviral peptide carbobenzoxy-D-phenylalanyl-L-phenylalanylglycine changes the average conformation of phospholipids in membranes. Biochemistry. 1993 Nov 16;32(45):12197-202. [PubMed:8218297 ]
  17. Kelsey DR, Flanagan TD, Young JE, Yeagle PL: Inhibition of Sendai virus fusion with phospholipid vesicles and human erythrocyte membranes by hydrophobic peptides. Virology. 1991 Jun;182(2):690-702. [PubMed:1850923 ]
  18. Kelsey DR, Flanagan TD, Young J, Yeagle PL: Peptide inhibitors of enveloped virus infection inhibit phospholipid vesicle fusion and Sendai virus fusion with phospholipid vesicles. J Biol Chem. 1990 Jul 25;265(21):12178-83. [PubMed:2165053 ]
  19. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]