Cysteinylglycine

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Cysteinylglycine
2D structure for Cysteinylglycine
Chemical Name	2-(2-amino-3-sulfanyl-propanoyl)aminoacetic acid
Chemical Formula	C₅H₁₀N₂O₃S
CAS Number	19246-18-5
Chemical Information	HMDB00078
Biochemical Taxonomy	Peptides
Functional Taxonomy	Not Available
Nutritional Taxonomy	Not Available
Metabolic Pathways	Glutathione Metabolism Prostaglandin and Leukotriene Metabolism
Biofluid Location	Blood Cerebrospinal Fluid (CSF) Saliva Urine
Tissue Location	Most Tissues
Normal Biofluid Concentrations	Blood: 13.6 +/- 3.6 uM Blood: 51.7 +/- 1.7 uM Blood: 51.8 +/- 4.9 uM Blood: 53.2 +/- 7.7 uM Blood: 54.0 +/- 18.8 uM Blood: 56.0 +/- 7.0 uM Blood: 57.5 +/- 5.9 uM Blood: 63.4 +/- 7.4 uM Cerebrospinal Fluid (CSF): 2.31 (0.99-3.62) uM Saliva: 0.00605 +/- 0.00512 uM Urine: 0.48 +/- 0.15 umol/mmol creatinine
Normal Tissue Concentrations	Not Available
Diseases / Conditions Related to Nutrition	Phenylketonuria (PKU)
Other (Monogenic Disorders)	Not Available
Abnormal Biofluid Concentrations	Blood (Phenylketonuria (PKU)): 6.0 (2.0-10.0) uM
Abnormal Tissue Concentrations	Not Available
Physiological Processes	Not Available

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Introduction

guidelines
Cysteinylglycine is a naturally occurring dipeptide. It is derived from the breakdown of glutathione (a tripeptide). In plasma, cysteinylglycine is in a reduced, oxidized and protein-bound form (aminothiol) and interact via redox and disulphide exchange reactions, in a dynamic system referred to as redox thiol status. (PMID 8642471) Spermatozoa of sub fertile men contain significantly higher thiol concentrations as compared with those of fertile men. The detrimental effect on embryo quality of a high homocysteine (Hcy, another member of the thiol group) concentration in the ejaculate and in follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome. (PMID 16556671) Rheumatoid arthritis (RA) is a chronic inflammatory disease which involves the synovial membrane of multiple diarthroidal joints causing damage to cartilage and bones. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols. (PMID 15895891) Imipenem (thienamycin formamidine), is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized. (PMID 15843241)