63039-46-3Relevant articles and documents
D-ALA-D-ALA-BASED DIPEPTIDES AS TOOLS FOR IMAGING PEPTIDOGLYCAN BIOSYNTHESIS
-
Paragraph 0186-0190, (2016/08/29)
Disclosed herein are compositions for assessing peptidoglycan biosynthesis in bacteria using modified dipeptides containing a bioorthogonal tag and applying novel post-labeling methods to label the bioorthogonal tag. The resultant, labeled peptidoglycan structures are amenable for identifying bacteria by microscopic visualization.
α-Propargyl amino acid-derived optically active novel substituted polyacetylenes: Synthesis, secondary structures, and responsiveness to ions
Sogawa, Hiromitsu,Shiotsuki, Masashi,Sanda, Fumio
experimental part, p. 2008 - 2018 (2012/07/13)
Novel optically active substituted acetylenes HCi￡ CCH 2CR1(CO2CH3)NHR2 [(S)-/(R)-1: R1 = H, R2 = Boc, (S)-2: R1 = CH3, R2 = Boc, (S)-3: R1 = H, R2 = Fmoc, (S)-4: R1 = CH3, R2 = Fmoc (Boc = tert-butoxycarbonyl, Fmoc = 9-fluorenylmethoxycarbonyl)] were synthesized from α-propargylglycine and α-propargylalanine, and polymerized with a rhodium catalyst to provide the polymers with number-average molecular weights of 2400-38,900 in good yields. Polarimetric, circular dichroism (CD), and UV-vis spectroscopic analyses indicated that poly[(S)-1], poly[(R)-1], and poly[(S)-4] formed predominantly one-handed helical structures both in polar and nonpolar solvents. Poly[(S)-1a] carrying unprotected carboxy groups was obtained by alkaline hydrolysis of poly[(S)-1], and poly[(S)-4b] carrying unprotected amino groups was obtained by removal of Fmoc groups of poly[(S)-4] using piperidine. Poly[(S)-1a] and poly[(S)-4b] also exhibited clear CD signals, which were different from those of the precursors, poly[(S)-1] and poly[(S)-4]. The solution-state IR measurement revealed the presence of intramolecular hydrogen bonding between the carbamate groups of poly[(S)-1] and poly[(S)-1a]. The plus CD signal of poly[(S)-1a] turned into minus one on addition of alkali hydroxides and tetrabutylammonium fluoride, accompanying the red-shift of λmax. The degree of λmax shift became large as the size of cation of the additive.
N6-(2-(R)-propargylglycyl)lysine as a clickable pyrrolysine mimic
Li, Xin,Fekner, Tomasz,Chan, Michael K.
supporting information; experimental part, p. 1765 - 1769 (2011/03/22)
Clickable copycat! Readily available dipeptide d-Pra-ε-Lys is identified using a modified fluorescence protein assay as a highly efficient clickable pyrrolysine mimic. It is shown to incorporate into calmodulin in high yield to provide a handle for labeling with anazide-containing coumarin.
Palladium-Catalyzed Cyclization Reactions of Acetylene-Containing Amino Acids
Wolf, Larissa B.,Tjen, Kim C. M. F.,Ten Brink, Hefziba T.,Blaauw, Richard H.,Hiemstra, Henk,Schoemaker, Hans E.,Rutjes, Floris P. J. T.
, p. 70 - 83 (2007/10/03)
Enantiomerically pure acetylene-containing α-amino acids were used as versatile starting materials for the synthesis of a variety of heterocycles via Pd-mediated cyclization reactions. Depending on the protecting group strategy, both the carboxylate and the amine function of the amino acids could participate in the cyclizations, thus giving rise to oxygen heterocycles (α-aminolactones) and nitrogen heterocycles (cyclic α-amino acid derivatives), respectively. Beside the straightforward cyclization, cyclization/cross-coupling reactions were also successfully carried out to provide the corresponding substituted cyclic amino acid derivatives.
Synthesis, properties and crystal structure of the tripeptide boc-L-prolyl-L-propargylglycyl-glycine methylester
Willisch, Hans,Hiller, Wolfgang,Hemmasi, Bahram,Bayer, Ernst
, p. 3947 - 3958 (2007/10/02)
Propargylglycine, as a powerful inhibitor of microbial growth, was built into a protected tripeptide with the sequence Pro-Pra-Gly. The peptide was employed to study its effects on the activity of prolyl 4-hydroxylase and the collagen biosynthesis. The Boc-protected tripeptide methylester was identified by mass spectrometry and NMR spectroscopy and its crystal structure was established by X-ray diffraction analysis.
