D-Lactic acid (ECMDB01311) (M2MDB000334)
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| Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 13:49:42 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:10 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | D-Lactic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | D-Lactic acid is the end product of the enzyme Glyoxalase ([EC:3.1.2.6] hydroxyacyl-glutathione hydrolase) which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate. (OMIM 138790) | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
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| Chemical Formula: | C3H6O3 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 90.0779 Monoisotopic: 90.031694058 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | JVTAAEKCZFNVCJ-UWTATZPHSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 10326-41-7 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-hydroxypropanoic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | (α)-lactate | |||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | C[C@@H](O)C(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Hydroxy acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Alpha hydroxy acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Alpha hydroxy acids and derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -1 | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 52.8 C | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid Water + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acid D-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8 N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid S-Lactoylglutathione + Water <> Glutathione + D-Lactic acid an electron-transfer-related quinone + D-Lactic acid > an electron-transfer-related quinol + Pyruvic acid NAD + D-Lactic acid < Hydrogen ion + NADH + Pyruvic acid D-Lactic acid + Hydrogen ion < Pyruvaldehyde + Water D-Lactic acid + NAD > Pyruvic acid + NADH D-Lactic acid > Pyruvaldehyde + Water N-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid D-Lactic acid <> Pyruvaldehyde + Water MurNAc-6-P + Water > D-Lactic acid + N-Acetylglucosamine 6-phosphate Pyruvaldehyde + Water > D-Lactic acid + Hydrogen ion N-Acetylmuramate 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid D-Lactic acid + 2 Hydrogen ion + an ubiquinol > Pyruvic acid + ubiquinone D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid D-Lactic acid <> Pyruvaldehyde + Water D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid D-Lactic acid <> Pyruvaldehyde + Water | |||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
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| KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
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| Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Hsieh, Chun Lung; Houng, Jer Yiing. Preparation of D-lactic acid from D,L-lactic acid ester using wheat germ or pancreatic lipase. U.S. (1997), 5 pp. | |||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | |||||||||||||||||||||||||||||||||||||||||||||||||||
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Enzymes
- General function:
- Involved in flavin adenine dinucleotide binding
- Specific function:
- First component of the membrane-bound D-lactate oxidase, which is believed to play an important role in the energization of the active transport of a variety of sugars and amino acids
- Gene Name:
- dld
- Uniprot ID:
- P06149
- Molecular weight:
- 64612
Reactions
| (R)-lactate + NAD(+) = pyruvate + NADH. |
- General function:
- Involved in hydrolase activity
- Specific function:
- Thiolesterase that catalyzes the hydrolysis of S-D- lactoyl-glutathione to form glutathione and D-lactic acid
- Gene Name:
- gloB
- Uniprot ID:
- P0AC84
- Molecular weight:
- 28434
Reactions
| S-(2-hydroxyacyl)glutathione + H(2)O = glutathione + a 2-hydroxy carboxylate. |
- General function:
- Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
- Specific function:
- Fermentative lactate dehydrogenase
- Gene Name:
- ldhA
- Uniprot ID:
- P52643
- Molecular weight:
- 36535
Reactions
| (R)-lactate + NAD(+) = pyruvate + NADH. |
- General function:
- Involved in carbon-oxygen lyase activity
- Specific function:
- Specifically catalyzes the cleavage of the D-lactyl ether substituent of MurNAc 6-phosphate, producing GlcNAc 6- phosphate and D-lactate. Is required for growth on MurNAc as the sole source of carbon and energy. Together with AnmK, is also required for the utilization of anhydro-N-acetylmuramic acid (anhMurNAc) either imported from the medium or derived from its own cell wall murein, and thus plays a role in cell wall recycling
- Gene Name:
- murQ
- Uniprot ID:
- P76535
- Molecular weight:
- 31220
Reactions
| N-acetylmuramate 6-phosphate + H(2)O = N-acetyl-D-glucosamine 6-phosphate + D-lactate. |
- General function:
- Not Available
- Specific function:
- Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus. Functions as a holding molecular chaperone (holdase) which stabilizes unfolding intermediates and rapidly releases them in an active form once stress has abated. Plays an important role in protecting cells from severe heat shock and starvation, as well as in acid resistance of stationary-phase cells. It uses temperature-induced exposure of structured hydrophobic domains to capture and stabilizes early unfolding and denatured protein intermediates under severe thermal stress. Catalyzes the conversion of methylglyoxal (MG) to D-lactate in a single glutathione (GSH)-independent step. It can also use phenylglyoxal as substrate. Glyoxalase activity protects cells against dicarbonyl stress. Displays an aminopeptidase activity that is specific against peptide substrates with alanine or basic amino acids (lysine, arginine) at N-terminus.
- Gene Name:
- hchA
- Uniprot ID:
- P31658
- Molecular weight:
- Not Available
Reactions
| (R)-lactate = methylglyoxal + H(2)O. |
| (R)-lactate = methylglyoxal + H(2)O. |
Transporters
- General function:
- Involved in lactate transmembrane transporter activity
- Specific function:
- Transports L-lactate across the membrane. Can also transport D-lactate and glycolate. Seems to be driven by a proton motive force
- Gene Name:
- lldP
- Uniprot ID:
- P33231
- Molecular weight:
- 59168
- General function:
- Involved in lactate transmembrane transporter activity
- Specific function:
- Transports glycolate across the membrane. Can also transport L-lactate and D-lactate. Seems to be driven by a proton motive force
- Gene Name:
- glcA
- Uniprot ID:
- Q46839
- Molecular weight:
- 58920
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368