| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:33:39 UTC |
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| Update date | 2017-01-19 02:36:43 UTC |
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| FoodComEx ID | PC000976 |
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| FoodDB Record | FDB021891 |
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| Chemical Information |
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| Name | Cysteinylglycine |
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| Description | Cysteinylglycine, also known as CG or cys-gly, 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. 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. Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. 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. It is derived from the breakdown of glutathione (a tripeptide). Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans. 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). Outside of the human body, Cysteinylglycine has been detected, but not quantified in, several different foods, such as garlics, sweet rowanberries, butternut squash, common oregano, and pepper (c. frutescens). This could make cysteinylglycine a potential biomarker for the consumption of these foods. Cysteinylglycine, with regard to humans, has been linked to the inborn metabolic disorder phenylketonuria. |
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| CAS Number | 19246-18-5 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Cys-Gly | hmdb | | L-Cysteinylglycine | hmdb | | N-cysteinyl Glycine | hmdb | | N-cysteinyl-Glycine | hmdb | | N-L-cysteinyl-Glycine | hmdb | | N-L-Cysteinylglycine | hmdb |
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| Chemical Formula | C5H10N2O3S |
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| IUPAC name | 2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid |
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| InChI Identifier | InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1 |
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| InChI Key | ZUKPVRWZDMRIEO-VKHMYHEASA-N |
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| Isomeric SMILES | N[C@@H](CS)C(=O)NCC(O)=O |
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| Average Molecular Weight | 178.21 |
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| Monoisotopic Molecular Weight | 178.041212886 |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | Dipeptides |
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| Alternative Parents | |
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| Substituents | - Alpha-dipeptide
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Cysteine or derivatives
- Alpha-amino acid or derivatives
- Amino acid or derivatives
- Amino acid
- Carboxamide group
- Secondary carboxylic acid amide
- Alkylthiol
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Organosulfur compound
- Primary aliphatic amine
- Primary amine
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Amine
- Organopnictogen compound
- Organic oxygen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 4 g |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Toronto Research Chemicals | C994770 |
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