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Record Information
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:28:45 UTC
Secondary Accession NumbersNone
Metabolite Identification
Common NameGlycylproline
DescriptionGlycylproline is an end product of collagen metabolism that is further cleaved by prolidase (EC; the resulting proline molecules are recycled into collagen or other proteins. Prolidase deficiency is a rare autosomal recessive disease characterized by chronic ulcerative dermatitis, mental retardation, frequent infections and massive urinary excretion of iminodipeptides. The disease has been confirmed to be due to hereditary prolidase deficiency. It has been reported that the activity of the enzyme against glycylproline (Gly-Pro) is almost totally deficient in patients with prolidase deficiency, whereas the activity against other substrates is not so deficient. Some patients with prolidase deficiency have a marked urinary excretion of the iminodipeptide Glycylproline. The urine from patients with pressure sores contains significantly more Glycylproline than the urine from the control. (PMID: 16009141 , 7629169 , 1536787 , 10582130 ).
  1. 1-(Aminoacetyl)proline
  2. 1-Glycyl-L-Proline
  3. 1-Glycylproline
  4. GLY-pro
  5. N-Glycyl-L-proline
  6. N-Glycylproline
Chemical FormulaC7H12N2O3
Average Molecular Weight172.1818
Monoisotopic Molecular Weight172.08479226
IUPAC Name1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid
Traditional Name1-(2-aminoacetyl)pyrrolidine-2-carboxylic acid
CAS Registry Number704-15-4
InChI Identifier
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
Sub ClassN/A
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • a dipeptide(Cyc)
  • Carboxamide Group
  • Carboxylic Acid
  • Primary Aliphatic Amine (Alkylamine)
  • Pyrrolidine
  • Pyrrolidine Carboxylic Acid
  • Tertiary Carboxylic Acid Amide
Direct ParentPeptides
StatusDetected and Quantified
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
Experimental Properties
Melting Point155 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility279 g/LALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.63ChemAxon
Rotatable Bond Count2ChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
UrineDetected and Quantified0.4 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.23 +/- 0.04 uMElderly (>65 years old)Both
Alzheimer's disease
Cerebrospinal Fluid (CSF)Detected and Quantified0.086 +/- 0.016 uMElderly (>65 years old)BothAlzheimer's disease details
UrineDetected and Quantified590.8 +/- 81.14 umol/mmol creatinineAdult (>18 years old)Not SpecifiedProlidase deficiency details
UrineDetected and Quantified0.0087 +/- 0.0016 umol/mmol creatinineElderly (>65 years old)BothAlzheimer's disease details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
Prolidase deficiency
  1. Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. Pubmed: 16120410
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022202
KNApSAcK IDNot Available
Chemspider ID71432
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00721
Metagene LinkHMDB00721
PubChem Compound79101
PDB IDNot Available
ChEBI ID356660
Synthesis ReferenceMaruyama, Susumu; Ichimura, Toshiaki; Otsuka, Tatsuo; Yamashita, Eiichi. Long-lasting antihypertensive agents and glycylproline manufactured from collagen and/or gelatin. Jpn. Kokai Tokkyo Koho (2005), 10 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  2. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  3. Barshop BA: Metabolomic approaches to mitochondrial disease: correlation of urine organic acids. Mitochondrion. 2004 Sep;4(5-6):521-7. Epub 2004 Sep 30. Pubmed: 16120410
  4. Krepela E, Kasafirek E, Vicar J, Kraml J: An assay of dipeptidyl peptidase IV activity in human serum and serum of pregnant women with glycyl-L-proline-1-naphthylamide and other glycyl-L-proline-arylamides as substrates. Physiol Bohemoslov. 1983;32(4):334-45. Pubmed: 6353449
  5. Liu G, Nakayama K, Sagara Y, Awata S, Yamashita K, Manabe M, Kodama H: Characterization of prolidase activity in erythrocytes from a patient with prolidase deficiency: comparison with prolidase I and II purified from normal human erythrocytes. Clin Biochem. 2005 Jul;38(7):625-31. Pubmed: 16009141
  6. Mock WL, Liu Y: Hydrolysis of picolinylprolines by prolidase. A general mechanism for the dual-metal ion containing aminopeptidases. J Biol Chem. 1995 Aug 4;270(31):18437-46. Pubmed: 7629169
  7. Berardesca E, Fideli D, Bellosta M, Dyne KM, Zanaboni G, Cetta G: Blood transfusions in the therapy of a case of prolidase deficiency. Br J Dermatol. 1992 Feb;126(2):193-5. Pubmed: 1536787
  8. Le J, Perier C, Peyroche S, Rascle F, Blanchon MA, Gonthier R, Frey J, Chamson A: Urine glycyl-L-proline increase and skin trophicity. Amino Acids. 1999;17(3):315-22. Pubmed: 10582130


General function:
Involved in cellular process
Specific function:
Splits dipeptides with a prolyl or hydroxyprolyl residue in the C-terminal position. Plays an important role in collagen metabolism because the high level of iminoacids in collagen
Gene Name:
Uniprot ID:
Molecular weight:
  1. Yuan J, Li T, Yin XB, Guo L, Jiang X, Jin W, Yang X, Wang E: Characterization of prolidase activity using capillary electrophoresis with tris(2,2'-bipyridyl)ruthenium(II) electrochemiluminescence detection and application to evaluate collagen degradation in diabetes mellitus. Anal Chem. 2006 May 1;78(9):2934-8. Pubmed: 16642978