L-Argininamide

L-Argininamide

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Category Others
Catalog number BBF-04739
CAS 2788-83-2
Molecular Weight 173.2
Molecular Formula C6H15N5O

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Specification

Synonyms Arginine amide
IUPAC Name (2S)-2-amino-5-(diaminomethylideneamino)pentanamide
Canonical SMILES C(CC(C(=O)N)N)CN=C(N)N
InChI InChI=1S/C6H15N5O/c7-4(5(8)12)2-1-3-11-6(9)10/h4H,1-3,7H2,(H2,8,12)(H4,9,10,11)/t4-/m0/s1
InChI Key ULEBESPCVWBNIF-BYPYZUCNSA-N

Reference Reading

1. Synthesis of the kyotorphin precursor benzoyl-L-tyrosine-L-argininamide with immobilized α-chymotrypsin in sequential batch with enzyme reactivation
Carola Bahamondes, Lorena Wilson, Claudia Bernal, Andrés Illanes, Gregorio Álvaro, Fanny Guzmán Biotechnol Prog. 2016 Jan-Feb;32(1):54-9. doi: 10.1002/btpr.2187. Epub 2015 Nov 6.
α-Chymotrypsin was immobilized in activated agarose support and the stability of the biocatalyst was assessed in three polar organic solvents, namely, ethanol, diglyme, and acetonitrile. Ethanol was the solvent in which the stability of the enzyme was higher and was then selected to perform the synthesis of the kyotorphin derivative benzoyl-tyrosine argininamide, evaluating enzyme reactivation after synthesis. Substrates for reaction were benzoyl tyrosine ethyl ester and argininamide, the reaction being performed under kinetic control. High conversion yield (85%) was obtained and the immobilized enzyme was successfully used in sequential batch reactor operation with enzyme reactivation after three batches.
2. Determination of L-argininamide based on water-soluble fluorescent conjugated polymer-aptamer
Hongliang Guan, Zhike He J Anal Methods Chem. 2013;2013:682134. doi: 10.1155/2013/682134. Epub 2013 Aug 20.
Water-soluble fluorescent conjugated polymer is a promising material which could be used as an optical platform in highly sensitive molecular sensors. In this paper, a simple label-free DNA sensor, which consisted of a poly(3-alkoxy-4-methylthiophene) and an aptamer, was used to detect L-argininamide (L-Arm). Due to the specific binding reaction between L-Arm and its aptamer, the proposed method can easily determinate the L-Arm through the recovery of fluorescence without any modification. Other ions or similar molecules had little effect on the detection. Moreover, there was a linear relationship between fluorescence intensity and the concentration of L-Arm. The detection limit of L-Arm was as low as 4.7 nM.
3. Binding of l-Argininamide to a DNA Aptamer: A Volumetric Study
Lutan Liu, Lora Stepanian, David N Dubins, Tigran V Chalikian J Phys Chem B. 2018 Aug 9;122(31):7647-7653. doi: 10.1021/acs.jpcb.8b03912. Epub 2018 Jul 31.
We use a combination of volumetric and spectroscopic techniques to characterize the binding of l-argininamide to its aptamer, the 24-base DNA hairpin 5'-d(GATCGAAACGTAGCGCCTTCGATC)-3'. The binding causes increases in volume, Δ V, and adiabatic compressibility, Δ KS, of 12 ± 7 cm3 mol-1 bar and (73 ± 8) × 10-4 cm3 mol-1 bar-1, respectively. These volumetric results combined with structural data reveal that the binding is accompanied by release of 73 ± 27 waters from the hydration shells of the interacting molecules to the bulk. We use the estimated change in hydration to estimate the hydration, Δ Shyd, and configurational, Δ Sconf, contributions to the binding entropy. The large and unfavorable change in configurational entropy, Δ Sconf, is nearly compensated by a favorable change in the hydration contribution, Δ Shyd.

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