Glycylglycylglycine

Common Name

Glycylglycylglycine Description

Glycylglycylglycine is found in fruits. Glycylglycylglycine is isolated from the seeds of Blighia sapida (akee apple) Glycylglycylglycine belongs to the family of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid moleclies (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Structure

Synonyms

Value Source (Gly)3ChEBI DiglycylglycineChEBI GGGChEBI Gly-gly-glyChEBI GlyGlyGlyChEBI N-(N-Glycylglycyl)glycineChEBI TriglycineChEBI (([(Aminoacetyl)amino]acetyl)amino)acetic acidHMDB Glycine, N-(N-glycylglycyl)- (8ci)(9ci)HMDB GLYCYL-glycyl-glycineHMDB GlycylpeptideHMDB N-(N-GLYCYLGLYCYL)-glycineHMDB GGG PeptideMeSH Triglycine slifateMeSH Diglycyl-glycineMeSH

Chemical Formlia

C₆H₁₁N₃O₄ Average Molecliar Weight

189.1692 Monoisotopic Molecliar Weight

189.074955855 IUPAC Name

2-[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid Traditional Name

[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid CAS Registry Number

556-33-2 SMILES

InChI Identifier

InChI Key

XKUKSGPZAADMRA-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Oligopeptides Alternative Parents

N-acyl-alpha amino acids

Alpha amino acid amides

Secondary carboxylic acid amides

Amino acids

Monocarboxylic acids and derivatives

Carboxylic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

Alpha-oligopeptide

N-acyl-alpha-amino acid

N-acyl-alpha amino acid or derivatives

Alpha-amino acid amide

N-substituted-alpha-amino acid

Alpha-amino acid or derivatives

Amino acid or derivatives

Carboxamide group

Amino acid

Secondary carboxylic acid amide

Monocarboxylic acid or derivatives

Carboxylic acid

Organonitrogen compound

Organic oxygen compound

Organic oxide

Primary aliphatic amine

Organic nitrogen compound

Carbonyl group

Amine

Organooxygen compound

Primary amine

Organopnictogen compound

Hydrocarbon derivative

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic compounds External Descriptors

tripeptide (CHEBI:63961 )

Ontology Status

Expected but not Quantified Origin

Endogenous

Food

Biofunction

Not Available Application

Nutrient

Cellliar locations

Cytoplasm

Extracellliar

Physical Properties State

Not Available Experimental Properties

Property Value Reference Melting Point246 °CNot Available Boiling PointNot AvailableNot Available Water Solubility58.5 mg/mL at 25 °CNot Available LogP-2.68Not Available

Predicted Properties

Property Value Source Water Solubility1.63 mg/mLALOGPS logP-3.1ALOGPS logP-4.1ChemAxon logS-2.1ALOGPS pKa (Strongest Acidic)3.71ChemAxon pKa (Strongest Basic)9.34ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area128.5 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity42.65 m³·mol^-1ChemAxon Polarizability17.72 ųChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-00di-2920000000-c79f40a9740fc25b3f1cView in MoNA GC-MS

GC-MS Spectrum – GC-MS (5 TMS)splash10-00di-3910000000-4555ddf2ff8c000d0010View in MoNA GC-MS

GC-MS Spectrum – GC-MS (4 TMS)splash10-00di-2900000000-624925570b3a64cc957dView in MoNA GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-00di-2900000000-c27bc3ac23a84247a718View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

Mass Spectrum (Electron Ionization)splash10-001i-9100000000-b943e0e1caf180c452cfView in MoNA 1D NMR

13C NMR SpectrumNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB000517 KNApSAcK ID

Not Available Chemspider ID

10688 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB29419 Metagene Link

HMDB29419 METLIN ID

Not Available PubChem Compound

11161 PDB ID

GGG ChEBI ID

63961

Product: Histamine (phosphate)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
2. Li J, Hidalgo IJ: Molecular modeling study of structural requirements for the oligopeptide transporter. J Drug Target. 1996;4(1):9-17. [PubMed:8798874 ]
3. Liu S, Edwards DS, Looby RJ, Poirier MJ, Rajopadhye M, Bourque JP, Carroll TR: Labeling cyclic glycoprotein IIb/IIIa receptor antagonists with 99mTc by the preformed chelate approach: effects of chelators on properties of [99mTc]chelator-peptide conjugates. Bioconjug Chem. 1996 Mar-Apr;7(2):196-202. [PubMed:8983341 ]
4. Hedwig GR, Hoiland H: Thermodynamic properties of peptide solutions. Part 11. Partial molar isentropic pressure coefficients in aqueous solutions of some tripeptides that model protein side-chains. Biophys Chem. 1994 Mar;49(2):175-81. [PubMed:8155817 ]
5. Lipowska M, Hansen L, Xu X, Marzilli PA, Taylor A Jr, Marzilli LG: New N(3)S donor ligand small peptide analogues of the N-mercaptoacetyl-glycylglycylglycine ligand in the clinically used Tc-99m renal imaging agent: evidence for unusual amide oxygen coordination by two new ligands. Inorg Chem. 2002 Jun 3;41(11):3032-41. [PubMed:12033915 ]
6. Bokatzian-Johnson SS, Stover ML, Dixon DA, Cassady CJ: Gas-phase deprotonation of the peptide backbone for tripeptides and their methyl esters with hydrogen and methyl side chains. J Phys Chem B. 2012 Dec 27;116(51):14844-58. doi: 10.1021/jp3113528. Epub 2012 Dec 14. [PubMed:23194315 ]
7. Rios A, Richard JP, Amyes TL: Formation and stability of peptide enolates in aqueous solution. J Am Chem Soc. 2002 Jul 17;124(28):8251-9. [PubMed:12105903 ]
8. El Aribi H, Rodriquez CF, Almeida DR, Ling Y, Mak WW, Hopkinson AC, Siu KW: Elucidation of fragmentation mechanisms of protonated Peptide ions and their products: a case study on glycylglycylglycine using density functional theory and threshold collision-induced dissociation. J Am Chem Soc. 2003 Jul 30;125(30):9229-36. [PubMed:15369379 ]
9. Poschet JF, Hammond SM, Fairclough PD: Characterisation of penicillin-G uptake in rabbit small-intestinal brush-border membrane vesicles. Biochim Biophys Acta. 1996 Jan 31;1278(2):233-40. [PubMed:8593281 ]
10. Rodriquez CF, Cunje A, Shoeib T, Chu IK, Hopkinson AC, Siu KW: Proton migration and tautomerism in protonated triglycine. J Am Chem Soc. 2001 Apr 4;123(13):3006-12. [PubMed:11457011 ]
11. Ma L, Yu P, Veerendra B, Rold TL, Retzloff L, Prasanphanich A, Sieckman G, Hoffman TJ, Volkert WA, Smith CJ: In vitro and in vivo evaluation of Alexa Fluor 680-bombesin[7-14]NH2 peptide conjugate, a high-affinity fluorescent probe with high selectivity for the gastrin-releasing peptide receptor. Mol Imaging. 2007 May-Jun;6(3):171-80. [PubMed:17532883 ]
12. Gunji H, Kochi H, Hiraiwa K: Comparison of kinetic property between human seminal and renal gamma-glutamyltransferase. Fukushima J Med Sci. 1994 Dec;40(2):119-32. [PubMed:7642163 ]
13. Tsukagoshi K, Sawanoi K, Nakajima R: Capillary electrophoretic system incorporating an UV/CL dual detector. Talanta. 2006 Feb 15;68(4):1071-5. doi: 10.1016/j.talanta.2005.06.070. Epub 2005 Aug 16. [PubMed:18970433 ]
14. Cheng J, Khin KT, Jensen GS, Liu A, Davis ME: Synthesis of linear, beta-cyclodextrin-based polymers and their camptothecin conjugates. Bioconjug Chem. 2003 Sep-Oct;14(5):1007-17. [PubMed:13129405 ]
15. Ye SJ, Armentrout PB: Absolute thermodynamic measurements of alkali metal cation interactions with a simple dipeptide and tripeptide. J Phys Chem A. 2008 Apr 24;112(16):3587-96. doi: 10.1021/jp710709j. Epub 2008 Mar 26. [PubMed:18363386 ]
16. Alves S, Correia JD, Santos I, Veerendra B, Sieckman GL, Hoffman TJ, Rold TL, Figueroa SD, Retzloff L, McCrate J, Prasanphanich A, Smith CJ: Pyrazolyl conjugates of bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)3]+ moiety. Nucl Med Biol. 2006 Jul;33(5):625-34. Epub 2006 May 2. [PubMed:16843837 ]
17. Asakura T, Takahashi N, Takada K, Inoue T, Ohkawa K: Drug conjugate of doxorubicin with glutathione is a potent reverser of multidrug resistance in rat hepatoma cells. Anticancer Drugs. 1997 Feb;8(2):199-203. [PubMed:9073316 ]
18. Koleva BB, Kolev TM, Spiteller M: Structural and spectroscopic analysis of hydrogensquarates of glycine-containing tripeptides. Biopolymers. 2006 Dec 5;83(5):498-507. [PubMed:16886213 ]
19. Downes CJ, Hedwig GR: Partial molar heat capacities of the peptides glycylglycylglycine, glycyl-L-alanylglycine and glycyl-DL-threonylglycine in aqueous solution over the temperature range 50 to 125 degrees C. Biophys Chem. 1995 Aug;55(3):279-88. [PubMed:17020871 ]
20. Martin NH, Loveless DM, Main KL, Pyles AK: Computation of through-space NMR shielding effects by functional groups common to peptides. J Mol Graph Model. 2006 Sep;25(1):1-9. Epub 2005 Nov 18. [PubMed:16300978 ]
21. Ogawa K, Mukai T, Arano Y, Ono M, Hanaoka H, Ishino S, Hashimoto K, Nishimura H, Saji H: Development of a rhenium-186-labeled MAG3-conjugated bisphosphonate for the palliation of metastatic bone pain based on the concept of bifunctional radiopharmaceuticals. Bioconjug Chem. 2005 Jul-Aug;16(4):751-7. [PubMed:16029015 ]
22. Danyi P, Varnagy K, Sovago I, Schon I, Sanna D, Micera G: Potentiometric and spectroscopic studies on the copper(II) complexes of peptide hormones containing disulfide bridges. J Inorg Biochem. 1995 Oct;60(1):69-78. [PubMed:7595472 ]
23. Chu IK, Shoeib T, Guo X, Rodriquez CF, Lau TC, Hopkinson AC, Siu KW: Characterization of the product ions from the collision-induced dissociation of argentinated peptides. J Am Soc Mass Spectrom. 2001 Feb;12(2):163-75. [PubMed:11212001 ]
24. Akao T, Kobashi K: Inhibitory effect of glycine on ethanol absorption from gastrointestinal tract. Biol Pharm Bull. 1995 Dec;18(12):1653-6. [PubMed:8787782 ]
25. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

PMID: 7908055

Common Name

Glycylglycylglycine Description

Glycylglycylglycine is found in fruits. Glycylglycylglycine is isolated from the seeds of Blighia sapida (akee apple) Glycylglycylglycine belongs to the family of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid moleclies (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Structure

Synonyms

Value Source (Gly)3ChEBI DiglycylglycineChEBI GGGChEBI Gly-gly-glyChEBI GlyGlyGlyChEBI N-(N-Glycylglycyl)glycineChEBI TriglycineChEBI (([(Aminoacetyl)amino]acetyl)amino)acetic acidHMDB Glycine, N-(N-glycylglycyl)- (8ci)(9ci)HMDB GLYCYL-glycyl-glycineHMDB GlycylpeptideHMDB N-(N-GLYCYLGLYCYL)-glycineHMDB GGG PeptideMeSH Triglycine slifateMeSH Diglycyl-glycineMeSH

Chemical Formlia

C₆H₁₁N₃O₄ Average Molecliar Weight

189.1692 Monoisotopic Molecliar Weight

189.074955855 IUPAC Name

2-[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid Traditional Name

[(Z)-{2-[(Z)-(2-amino-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino]acetic acid CAS Registry Number

556-33-2 SMILES

InChI Identifier

InChI Key

XKUKSGPZAADMRA-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Carboxylic acids and derivatives Direct Parent

Oligopeptides Alternative Parents

N-acyl-alpha amino acids

Alpha amino acid amides

Secondary carboxylic acid amides

Amino acids

Monocarboxylic acids and derivatives

Carboxylic acids

Organopnictogen compounds

Organic oxides

Monoalkylamines

Hydrocarbon derivatives

Carbonyl compounds

Substituents

Alpha-oligopeptide

N-acyl-alpha-amino acid

N-acyl-alpha amino acid or derivatives

Alpha-amino acid amide

N-substituted-alpha-amino acid

Alpha-amino acid or derivatives

Amino acid or derivatives

Carboxamide group

Amino acid

Secondary carboxylic acid amide

Monocarboxylic acid or derivatives

Carboxylic acid

Organonitrogen compound

Organic oxygen compound

Organic oxide

Primary aliphatic amine

Organic nitrogen compound

Carbonyl group

Amine

Organooxygen compound

Primary amine

Organopnictogen compound

Hydrocarbon derivative

Aliphatic acyclic compound

Molecliar Framework

Aliphatic acyclic compounds External Descriptors

tripeptide (CHEBI:63961 )

Ontology Status

Expected but not Quantified Origin

Endogenous

Food

Biofunction

Not Available Application

Nutrient

Cellliar locations

Cytoplasm

Extracellliar

Physical Properties State

Not Available Experimental Properties

Property Value Reference Melting Point246 °CNot Available Boiling PointNot AvailableNot Available Water Solubility58.5 mg/mL at 25 °CNot Available LogP-2.68Not Available

Predicted Properties

Property Value Source Water Solubility1.63 mg/mLALOGPS logP-3.1ALOGPS logP-4.1ChemAxon logS-2.1ALOGPS pKa (Strongest Acidic)3.71ChemAxon pKa (Strongest Basic)9.34ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count7ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area128.5 ŲChemAxon Rotatable Bond Count5ChemAxon Refractivity42.65 m³·mol^-1ChemAxon Polarizability17.72 ųChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-00di-2920000000-c79f40a9740fc25b3f1cView in MoNA GC-MS

GC-MS Spectrum – GC-MS (5 TMS)splash10-00di-3910000000-4555ddf2ff8c000d0010View in MoNA GC-MS

GC-MS Spectrum – GC-MS (4 TMS)splash10-00di-2900000000-624925570b3a64cc957dView in MoNA GC-MS

GC-MS Spectrum – GC-MS (3 TMS)splash10-00di-2900000000-c27bc3ac23a84247a718View in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

Mass Spectrum (Electron Ionization)splash10-001i-9100000000-b943e0e1caf180c452cfView in MoNA 1D NMR

13C NMR SpectrumNot Available

Biological Properties Cellliar Locations

Cytoplasm

Extracellliar

Biofluid Locations

Not Available Tissue Location

Not Available Pathways

Not Available Normal Concentrations Not Available Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

Not Available DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

FDB000517 KNApSAcK ID

Not Available Chemspider ID

10688 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Not Available NuGOwiki Link

HMDB29419 Metagene Link

HMDB29419 METLIN ID

Not Available PubChem Compound

11161 PDB ID

GGG ChEBI ID

63961

Product: Histamine (phosphate)

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. Wang P, Wesdemiotis C, Kapota C, Ohanessian G: The sodium ion affinities of simple di-, tri-, and tetrapeptides. J Am Soc Mass Spectrom. 2007 Mar;18(3):541-52. Epub 2006 Dec 8. [PubMed:17157529 ]
2. Li J, Hidalgo IJ: Molecular modeling study of structural requirements for the oligopeptide transporter. J Drug Target. 1996;4(1):9-17. [PubMed:8798874 ]
3. Liu S, Edwards DS, Looby RJ, Poirier MJ, Rajopadhye M, Bourque JP, Carroll TR: Labeling cyclic glycoprotein IIb/IIIa receptor antagonists with 99mTc by the preformed chelate approach: effects of chelators on properties of [99mTc]chelator-peptide conjugates. Bioconjug Chem. 1996 Mar-Apr;7(2):196-202. [PubMed:8983341 ]
4. Hedwig GR, Hoiland H: Thermodynamic properties of peptide solutions. Part 11. Partial molar isentropic pressure coefficients in aqueous solutions of some tripeptides that model protein side-chains. Biophys Chem. 1994 Mar;49(2):175-81. [PubMed:8155817 ]
5. Lipowska M, Hansen L, Xu X, Marzilli PA, Taylor A Jr, Marzilli LG: New N(3)S donor ligand small peptide analogues of the N-mercaptoacetyl-glycylglycylglycine ligand in the clinically used Tc-99m renal imaging agent: evidence for unusual amide oxygen coordination by two new ligands. Inorg Chem. 2002 Jun 3;41(11):3032-41. [PubMed:12033915 ]
6. Bokatzian-Johnson SS, Stover ML, Dixon DA, Cassady CJ: Gas-phase deprotonation of the peptide backbone for tripeptides and their methyl esters with hydrogen and methyl side chains. J Phys Chem B. 2012 Dec 27;116(51):14844-58. doi: 10.1021/jp3113528. Epub 2012 Dec 14. [PubMed:23194315 ]
7. Rios A, Richard JP, Amyes TL: Formation and stability of peptide enolates in aqueous solution. J Am Chem Soc. 2002 Jul 17;124(28):8251-9. [PubMed:12105903 ]
8. El Aribi H, Rodriquez CF, Almeida DR, Ling Y, Mak WW, Hopkinson AC, Siu KW: Elucidation of fragmentation mechanisms of protonated Peptide ions and their products: a case study on glycylglycylglycine using density functional theory and threshold collision-induced dissociation. J Am Chem Soc. 2003 Jul 30;125(30):9229-36. [PubMed:15369379 ]
9. Poschet JF, Hammond SM, Fairclough PD: Characterisation of penicillin-G uptake in rabbit small-intestinal brush-border membrane vesicles. Biochim Biophys Acta. 1996 Jan 31;1278(2):233-40. [PubMed:8593281 ]
10. Rodriquez CF, Cunje A, Shoeib T, Chu IK, Hopkinson AC, Siu KW: Proton migration and tautomerism in protonated triglycine. J Am Chem Soc. 2001 Apr 4;123(13):3006-12. [PubMed:11457011 ]
11. Ma L, Yu P, Veerendra B, Rold TL, Retzloff L, Prasanphanich A, Sieckman G, Hoffman TJ, Volkert WA, Smith CJ: In vitro and in vivo evaluation of Alexa Fluor 680-bombesin[7-14]NH2 peptide conjugate, a high-affinity fluorescent probe with high selectivity for the gastrin-releasing peptide receptor. Mol Imaging. 2007 May-Jun;6(3):171-80. [PubMed:17532883 ]
12. Gunji H, Kochi H, Hiraiwa K: Comparison of kinetic property between human seminal and renal gamma-glutamyltransferase. Fukushima J Med Sci. 1994 Dec;40(2):119-32. [PubMed:7642163 ]
13. Tsukagoshi K, Sawanoi K, Nakajima R: Capillary electrophoretic system incorporating an UV/CL dual detector. Talanta. 2006 Feb 15;68(4):1071-5. doi: 10.1016/j.talanta.2005.06.070. Epub 2005 Aug 16. [PubMed:18970433 ]
14. Cheng J, Khin KT, Jensen GS, Liu A, Davis ME: Synthesis of linear, beta-cyclodextrin-based polymers and their camptothecin conjugates. Bioconjug Chem. 2003 Sep-Oct;14(5):1007-17. [PubMed:13129405 ]
15. Ye SJ, Armentrout PB: Absolute thermodynamic measurements of alkali metal cation interactions with a simple dipeptide and tripeptide. J Phys Chem A. 2008 Apr 24;112(16):3587-96. doi: 10.1021/jp710709j. Epub 2008 Mar 26. [PubMed:18363386 ]
16. Alves S, Correia JD, Santos I, Veerendra B, Sieckman GL, Hoffman TJ, Rold TL, Figueroa SD, Retzloff L, McCrate J, Prasanphanich A, Smith CJ: Pyrazolyl conjugates of bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)3]+ moiety. Nucl Med Biol. 2006 Jul;33(5):625-34. Epub 2006 May 2. [PubMed:16843837 ]
17. Asakura T, Takahashi N, Takada K, Inoue T, Ohkawa K: Drug conjugate of doxorubicin with glutathione is a potent reverser of multidrug resistance in rat hepatoma cells. Anticancer Drugs. 1997 Feb;8(2):199-203. [PubMed:9073316 ]
18. Koleva BB, Kolev TM, Spiteller M: Structural and spectroscopic analysis of hydrogensquarates of glycine-containing tripeptides. Biopolymers. 2006 Dec 5;83(5):498-507. [PubMed:16886213 ]
19. Downes CJ, Hedwig GR: Partial molar heat capacities of the peptides glycylglycylglycine, glycyl-L-alanylglycine and glycyl-DL-threonylglycine in aqueous solution over the temperature range 50 to 125 degrees C. Biophys Chem. 1995 Aug;55(3):279-88. [PubMed:17020871 ]
20. Martin NH, Loveless DM, Main KL, Pyles AK: Computation of through-space NMR shielding effects by functional groups common to peptides. J Mol Graph Model. 2006 Sep;25(1):1-9. Epub 2005 Nov 18. [PubMed:16300978 ]
21. Ogawa K, Mukai T, Arano Y, Ono M, Hanaoka H, Ishino S, Hashimoto K, Nishimura H, Saji H: Development of a rhenium-186-labeled MAG3-conjugated bisphosphonate for the palliation of metastatic bone pain based on the concept of bifunctional radiopharmaceuticals. Bioconjug Chem. 2005 Jul-Aug;16(4):751-7. [PubMed:16029015 ]
22. Danyi P, Varnagy K, Sovago I, Schon I, Sanna D, Micera G: Potentiometric and spectroscopic studies on the copper(II) complexes of peptide hormones containing disulfide bridges. J Inorg Biochem. 1995 Oct;60(1):69-78. [PubMed:7595472 ]
23. Chu IK, Shoeib T, Guo X, Rodriquez CF, Lau TC, Hopkinson AC, Siu KW: Characterization of the product ions from the collision-induced dissociation of argentinated peptides. J Am Soc Mass Spectrom. 2001 Feb;12(2):163-75. [PubMed:11212001 ]
24. Akao T, Kobashi K: Inhibitory effect of glycine on ethanol absorption from gastrointestinal tract. Biol Pharm Bull. 1995 Dec;18(12):1653-6. [PubMed:8787782 ]
25. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

PMID: 7908055