PMID: 43840Jan 1, 1979

Formation of aminosuccinyl peptides during acidolytic deprotection followed by their transformation to piperazine-2,5-dione derivatives in neutral media

International Journal of Peptide and Protein Research
I Schön, L Kisfaludy

Abstract

Prolonged acidic treatment of Boc-Leu-Asp(OBut)-Phe-NH2 with 4N HCl in acetic acid resulted in H-Leu-Asc-Phe-NH2 . HCl(Asc, aminosuccinyl), which transformed partially to cyclo[Leu-Asp(Phe-NH2)] during its purification by column chromatography on silica gel with a mixture of ethyl acetate/pyridine/acetic acid/water = 60:20:6:11, i.e. in neutral medium. Examination of the imide formation was extended to different reaction conditions (no imide derivative was detected in trifluoroacetic acid), to several protected derivatives of L-aspartyl-L-phenylalaninamide and to tripeptides containing an aspartyl residue in the middle position. It was clearly demonstrated that in strongly acidic media the imide derivatives are directly formed from the aspartyl peptides containing a free beta-carboxyl group. The influence of the C-terminal residue was greater than the N-terminal on both the rate of formation of the imide and its further transformation to piperazine-2,5-dione derivative. In aqueous ethanol the X-Asc-Y-NH2 (X, Pro, Leu; Y, Gly, Ala, Val, Phg, Phe) containing N-terminal proline are more readily transformed to piperazine-2,5-dione derivatives, but compared to simple proline dipeptides the rate of this transformation is relatively s...Continue Reading

References

Sep 1, 1981·Biopolymers·H Yajima, N Fujii
Sep 1, 1981·International Journal of Peptide and Protein Research·H C BeyermanD Voskamp
Jul 1, 1996·International Journal of Peptide and Protein Research·K A HigginsM T Hearn
May 11, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Panagiotis StathopoulosVassilios Tsikaris
Jul 1, 1983·International Journal of Peptide and Protein Research·I SchönB Hegedüs
Feb 18, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·Peter M Fischer
Sep 14, 2007·Journal of Peptide Science : an Official Publication of the European Peptide Society·Helga Süli-VarghaJanez Ilas
May 1, 1990·Biological Chemistry Hoppe-Seyler·V M RobsonF Ng
Apr 1, 1987·International Journal of Peptide and Protein Research·S KiyamaH Yajima
Jul 17, 2019·Journal of Peptide Science : an Official Publication of the European Peptide Society·Daniel SamsonGünther Loidl

Citations

Feb 1, 1978·International Journal of Peptide and Protein Research·G Moore, D McMaster
Aug 1, 1978·Hoppe-Seyler's Zeitschrift für physiologische Chemie·L KisfaludyV Varró
Aug 1, 1978·Hoppe-Seyler's Zeitschrift für physiologische Chemie·I SchönV Varró
Jun 11, 1975·Journal of the American Chemical Society·S Sano, S Kawanishi
Aug 22, 1975·The Journal of Organic Chemistry·M Bodanszky, S Natarajan
Apr 4, 1973·Journal of the American Chemical Society·M BodanszkyA Bodanszky
May 3, 1972·Journal of the American Chemical Society·G W Kenner, J H Seely
Jan 1, 1966·Chemische Berichte·E Wünsch, A Zwick
Feb 1, 1967·Journal of the American Chemical Society·M Bodanszky, N J Williams

Related Concepts

Dione
Ethanol
Pyridines
Piperazine
Derivatives
Ethanol Measurement
Carboxy-Terminal Amino Acid
Piperazines
Chromatography
Imides

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Sexual Dimorphism in Neurodegeneration

There exist sex differences in neurodevelopmental and neurodegenerative disorders. For instance, multiple sclerosis is more common in women, whereas Parkinson’s disease is more common in men. Here is the latest research on sexual dimorphism in neurodegeneration

HLA Genetic Variation

HLA genetic variation has been found to confer risk for a wide variety of diseases. Identifying these associations and understanding their molecular mechanisms is ongoing and holds promise for the development of therapeutics. Find the latest research on HLA genetic variation here.

Super-resolution Microscopy

Super-resolution microscopy is the term commonly given to fluorescence microscopy techniques with resolutions that are not limited by the diffraction of light. Here are the latest discoveries pertaining to super-resolution microscopy.

Genetic Screens in iPSC-derived Brain Cells

Genetic screening is a critical tool that can be employed to define and understand gene function and interaction. This feed focuses on genetic screens conducted using induced pluripotent stem cell (iPSC)-derived brain cells.

Brain Lower Grade Glioma

Low grade gliomas in the brain form from oligodendrocytes and astrocytes and are the slowest-growing glioma in adults. Discover the latest research on these brain tumors here.

CD4/CD8 Signaling

Cluster of differentiation 4 and 8 (CD8 and CD8) are glycoproteins founds on the surface of immune cells. Here is the latest research on their role in cell signaling pathways.

Alignment-free Sequence Analysis Tools

Alignment-free sequence analyses have been applied to problems ranging from whole-genome phylogeny to the classification of protein families, identification of horizontally transferred genes, and detection of recombined sequences. Here is the latest research.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.