Pyroglutamic acid: a unique chiral synthon

Panday, Sharad Kumar; Prasad, J. S.; Dikshit, Dinesh K.

doi:10.1016/j.tetasy.2009.06.011

Cited by 75 publications

(26 citation statements)

References 156 publications

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“…Although pGlu helps the separation and has applications in the chemical industry, 18,19 ideally Glu should be recovered from pGlu as the former can be used for making chemicals. 8,30 Since the conversion of Glu to pGlu is reversible in water and pH-depended, 27 the recovery of Glu from pGlu was achieved by hydrolysis using acid (H 2 SO 4 ) or base (NaOH) (Fig.…”

Section: Hydrolysis Of Pglu To Glumentioning

confidence: 99%

“…Then pGlu can be isolated and converted back to Glu. While pGlu has applications for chiral synthesis and as a chemical, 18,19 by carrying out conversion and separation to produce Glu and Asp, more possibilities for the utilization of the AAs could be achieved. However, at the high temperatures required for reaction the deamination of Asp to fumaric acid (FUM) could also take place.…”

Section: Introductionmentioning

confidence: 99%

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Separation of L‐aspartic acid and L‐glutamic acid mixtures for use in the production of bio‐based chemicals

Teng

Scott

Sanders

2012

J of Chemical Tech & Biotech

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BACKGROUND: Amino acids are promising feedstocks for the chemical industry due to their chemical functionality. They can be obtained by the hydrolysis of potentially inexpensive protein streams such as the byproduct of biofuel production. However, individual amino acids are required before they can be used for the further production of chemicals. Here, the separation of L‐aspartic acid (Asp) and L‐glutamic acid (Glu) mixture, which can be isolated from protein hydrolysis solutions at low pH or from electrodialysis of complex amino acid mixtures, was studied.RESULTS: Glu was converted into L‐pyroglutamic acid (pGlu) which can be separated from the mixture of Asp and Glu due to its higher solubility in water. The conversion was carried out under aqueous or melt conditions. Under aqueous conditions, the conversion was studied as a factor of time, temperature and the amount of Glu. The conversion was specific with high yield and not effected by Asp. After pGlu was separated from Asp and residual Glu by solubility difference, it can be transferred back to Glu through hydrolysis.CONCLUSION: The conversion of Glu to pGlu is specific and can be applied to separation Asp and Glu for their use in the production of bio‐based chemicals. Copyright © 2012 Society of Chemical Industry

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Section: Hydrolysis Of Pglu To Glumentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Separation of L‐aspartic acid and L‐glutamic acid mixtures for use in the production of bio‐based chemicals

Teng

Scott

Sanders

2012

J of Chemical Tech & Biotech

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“…To allow the use of inexpensive natural compounds that are capable of forming imidic bonds, the possibility of utilizing pyroglutamic acid (pGlu) as a pseudoproline moiety was investigated. [8] Although pGlu is available in both configurations at low price, it is usually present in polypeptide chains only as an Nterminal amino acid, owing to the low reactivity of the nitrogen, and very few examples of nitrogen acylation have been described. [9] Unfortunately, the derivatization of pyroglutamic acid proved to be quite difficult (see Section 1.4) because it is an amide, so 2-carboxyoxazolidin-2-ones and 2-carboxyimidazolidin-2-ones were synthesized.…”

Section: Preparation Of Oxazolidin-2-ones and Related Moleculesmentioning

confidence: 99%

Foldamers Based on Oxazolidin‐2‐ones

2011

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Foldamers are artificial molecules capable of organization into well defined secondary structures such as helixes, β sheets and turns. The essential requirement for an oligomer to qualify for inclusion in the foldamer family is to possess a well defined, repetitive secondary structure, imparted by conformational restrictions imposed by the monomeric unit. These compounds may be composed of subunits of any kind, but most of them contain unusual amino acids and/or aromatic units. We describe the synthesis, the conformation analysis and the physical properties (in the solid state) of pseudopeptide foldamers containing imido‐type functions, obtained by coupling the nitrogen of a 4‐carboxy oxazolidin‐2‐one unit with the carboxylic acid moiety of the next unit, which may be another 4‐carboxy oxazolidin‐2‐one or an amino acid. Such an imido‐type function is characterized by a nitrogen atom connected both to an endocyclic and to an exocyclic carbonyl group, and tends always to adopt the trans conformation. As a consequence of this remarkable property, which causes local constraint, these imido‐type oligomers are forced to fold in ordered conformations. In combination with interactions of other kinds (H bond, apolar interactions, etc.), these lead to the formation of supramolecular materials. The synthetic approach is highly tuneable with endless variations, so materials with required properties may be prepared “on demand”, simply by changing the design and the synthesis.

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“…Our retrosynthetic analysis advocates for (S)-pyroglutaminol (2) (Scheme 2) as the chiral starting synthon, which is readily obtained from (S)-pyroglutamate. [41] This strategy will secure the stereochemical configuration of the a-amino acid functionality and furthermore, as the key step, the 2,3-transconfiguration at C3 ring carbon may be fully controlled by an addition of a suitable cuprate to the protected enone 4.…”

Section: Compdmentioning

confidence: 99%

Rational Design, Synthesis and Pharmacological Evaluation of the (2R)‐ and (2S)‐Stereoisomers of 3‐(2‐Carboxypyrrolidinyl)‐2‐methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors

et al. 2011

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In this paper we describe the rational design, synthesis and pharmacological evaluation of two new stereoisomeric (S)-glutamate (Glu) analogues. The rational design was based on hybrid structures of the natural product kainic acid, a synthetic analogue CPAA and the high-affinity Glu analogue SYM2081. Pharmacological evaluation of the two stereoisomers revealed that one stereoisomer showed a subtype selectivity profile with low micromolar affinity for GluK1 and GluK3 and a 10- to 15-fold lower affinity for GluK2. The other stereoisomer displayed full selectivity for the KA over AMPA and NMDA receptors (GluK1-3: 0.39, 0.51 and 0.099 µM, respectively).

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Pyroglutamic acid: a unique chiral synthon

Cited by 75 publications

References 156 publications

Separation of L‐aspartic acid and L‐glutamic acid mixtures for use in the production of bio‐based chemicals

Separation of L‐aspartic acid and L‐glutamic acid mixtures for use in the production of bio‐based chemicals

Foldamers Based on Oxazolidin‐2‐ones

Rational Design, Synthesis and Pharmacological Evaluation of the (2R)‐ and (2S)‐Stereoisomers of 3‐(2‐Carboxypyrrolidinyl)‐2‐methyl Acetic Acid as Ligands for the Ionotropic Glutamate Receptors

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