140681-94-3Relevant academic research and scientific papers
Reversible Folding of a β-Hairpin Peptide by a Metal-Chelating Amino Acid
Reutzel, Jan,Diogo, Timm M.,Geyer, Armin
, p. 8450 - 8456 (2017)
5-(1-Hydroxy-pyridin-2(1H)-onyl)-l-alanine (Hop) is a N-hydroxy-1,2-pyridone functionalized α-amino acid with the desired metal-chelating properties of DOPA (3,4-dihydroxy phenylalanine) but without its unwanted redox activity. The Fmoc-protected amino acid Fmoc-l-Hop(tBu)-OH (11) was synthesized from glycine phosphonate followed by enzymatic hydrolysis of the methyl ester yielding the Hop l-isomer in 96 % ee. The amino acid 11 is used in automated peptide synthesis for the assembly of a 14mer β-hairpin peptide with the sequence [dsb1, 14]H-CHXETGKHGHKLVC-OH (X=W, l-Hop). While the 10 π electron containing indole side chain of l-Trp in peptide 14 completes the formation of a hydrophobic cluster and results in 90 % folding, the folded fraction is significantly decreased to approximately 30 % for the 6 π electron l-Hop side chain in peptide 16. Metal chelation of Ga3+ reconstitutes the folding of 16 to above 60 % due to the formation of the Ga(16)3 trimer. The chelation process of 16 is monitored by NMR spectroscopy and the subsequent release of Ga3+ by a competitive metal chelator exemplifies the reversible oligomerization of peptide epitopes by metal chelation, bearing the opportunity to synthesize protein-sized aggregates on the basis of reversible chemistry in water.
CALCITONIN GENE RELATED PEPTIDE RECEPTOR ANTAGONISTS
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Page 164-165, (2010/02/04)
The presnt invention relates to compounds of Formula (I), as antagonists of calcitonin gene-related peptide receptors ("CGRP-receptor"), pharmaceutical compositions comprising them, methods for identifying them, methods of treatment using them and their use in therapy for treatment of neurogenic vasodilation, neurogenic inflammation, migraine and other headaches, thermal injury, circulatory shock, flushing associated with menopause, airway inflammatory diseases, such as asthma and chronic obstructive pulmonary disease (COPD), and other conditions the treatment of which can be effected by the antagonism of CGRP-receptors.
New amino acids from the poisonous mushroom Clitocybe acromelalga
Yamano, Kimiaki,Shirahama, Haruhisa
, p. 1457 - 1464 (2007/10/02)
New amino acids, L-3-(2-carboxy-4-pyrrolyl)-alanine (1) and L-3-(2-oxo-5-pyridyl)-alanine (2), were isolated from Clitocybe acromelalga and their structures were deduced by spectral data and biogenesis and confirmed by syntheses. Stizolobic acid (5) was also found in this fungus.
