A Facile Conversion of Amino Acids to Guanidino Acids

Miller, Audrey; Bischoff, Judith J.

doi:10.1055/s-1986-31777

Cited by 70 publications

(33 citation statements)

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“…2). In the spectra of GCS, the strong peaks at 1639, 1535, and 1380 cm −1 suggested that guanidinylation reaction had been successful 24. In the spectra of CGH, these peaks shifted to higher frequency 1656, 1557, 1383 cm −1 .…”

Section: Resultsmentioning

confidence: 95%

Preparation and anti‐TMV activity of guanidinylated chitosan hydrochloride

Lin

et al. 2009

J of Applied Polymer Sci

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In this study, guanidinylated chitosan hydrochloride (GCH) was synthesized and its structure was characterized by UV-vis and FTIR. The degree of substitution of guanidinylated chitosan was confirmed by elemental analysis. In vitro antiviral activity of guanidinium derivative on local infection and systemic infection of tobacco mosaic virus (TMV) inoculated were evaluated by semileaf method using different modes of GCH application and antiserum assay. Meanwhile, the morphological characteristic of virus treated by GCH was performed by transmission electron microscope. The results showed that GCH had better antiviral activity than chitosan. The average inhibitory rate of GCH on local infection was 84%, which was much higher than that of chitosan hydrochloride. It was shown that the guanidinylated chitosan was an efficient passivator, and its antiviral effect decreased after mechanical inoculation. The guanidinylated chitosan increased the resistance of plant against TMV and decreased the infection of the virus. The electron microscope photograph exhibited that GCH not only directly altered the configuration of TMV but also congregated and reduced the virus.

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Section: Resultsmentioning

confidence: 95%

Preparation and anti‐TMV activity of guanidinylated chitosan hydrochloride

Lin

et al. 2009

J of Applied Polymer Sci

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“…Guanidino analogs, guanidinoacetic acid (1) 3-guanidinopropionic acid (2), 4-guanidinobutanoic acid (3), 2-guanidinoethanesulfinic acid (4) (S)-2-guanidinopropanoic acid (5), (±)-2-guanidinopropanoic acid (6), (S)-2-guanidino butyricacid (7), (S)-2-guanidino-3-hydroxypropanoic acid (8), (S)-2-guanidino-3-methylbutyric acid (9), (2S,3R)-2-amino-3-hydroxybutyric acid (10), (S)-2-guanidino-2-(4-hydroxyphenyl) acetic acid (11) and creatine (12) were synthesized in house using established methodologies [25][26][27]. All other chemicals were obtained from SigmaAldrich (St Louis, MO, USA) unless otherwise stated.…”

Section: Methodsmentioning

confidence: 99%

Guanidino Acids Act as ρ1 GABAC Receptor Antagonists

et al. 2009

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GABA(C) receptors play a role in myopia, memory-related disorders and circadian rhythms signifying a need to develop potent and selective agents for this class of receptors. Guanidino analogs related to glycine, beta-alanine and taurine were evaluated at human rho(1)GABA(C) receptors expressed in Xenopus oocytes using 2-electrode voltage clamp methods. Of the 12 analogs tested, 8 analogs were active as antagonists and the remaining were inactive. (S)-2-guanidinopropionic acid (IC(50) = 2.2 microM) and guanidinoacetic acid (IC(50) = 5.4 microM; K (B) = 7.75 microM [pK (B) = 5.11 +/- 0.06]) were the most potent being competitive antagonists at this receptor. In contrast, the beta-alanine and GABA guanidino analogs showed reduced activity, indicating the distance between the carboxyl carbon and terminal nitrogen of the guanidino group is critical for activity. Substituting the C2-position of guanidinoacetic acid with various alkyl groups reduced activity indicating that steric effects may impact on activity. The results of this study contribute to the structure-activity-relationship profile required in developing novel therapeutic agents.

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“…The peak at 1314 cm −1 was assigned to the stretching vibration of CN, and the new stronger peak at 1069 cm −1 could be associated with the stretching vibration of CNC. The peaks at 1634, 1522, and 1378 cm −1 in the CSGH spectrum indicated the successful guanidinylation on chitosan …”

Section: Resultsmentioning

confidence: 94%

“…The peaks at 1634, 1522, and 1378 cm 21 in the CSGH spectrum indicated the successful guanidinylation on chitosan. 28…”

Section: Ftirmentioning

confidence: 99%

Microwave‐assisted synthesis of chitosan biguanidine hydrochloride and its antioxidant activity in vitro

Liu

Jin

et al. 2016

J of Applied Polymer Sci

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Chitosan biguanidine hydrochloride (CSGH) was synthesized by guanidinylation of chitosan hydrochloride (CSH) under microwave irradiation and characterized by Fourier transform infrared spectroscopy, gel permeation chromatography, and element analysis. The antioxidant activity of CSGH was evaluated by both chemical and cellular methods. The results showed that CSGH was better than CSH but slightly inferior to ascorbic acid (Vc) for scavenging 2,2‐diphenyl‐1‐picryl‐hydrazyl (DPPH) free radicals, and the DPPH• scavenging ability of CSGH was dose‐dependent. However, cell experiments indicated CSGH had a superior repairing effect on oxidatively damaged cells. The intervention of CSGH could excellently recover the cell morphology, decrease the level of malondialdehyde, and enhance the activity of superoxide dismutase and glutathione peroxidase. CSGH could be a potential antioxidant reagent, and its antioxidant activity was reflected not only in scavenging the free radicals but also in regulating the oxidation/antioxidation balance of damaged cells. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 43570.

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A Facile Conversion of Amino Acids to Guanidino Acids

Cited by 70 publications

References 0 publications

Preparation and anti‐TMV activity of guanidinylated chitosan hydrochloride

Preparation and anti‐TMV activity of guanidinylated chitosan hydrochloride

Guanidino Acids Act as ρ1 GABAC Receptor Antagonists

Microwave‐assisted synthesis of chitosan biguanidine hydrochloride and its antioxidant activity in vitro

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