Conversion of carboxyl groups of mucopolysaccharides into amides of amino acid esters

Danishefsky, I.; Siskovic, E.

doi:10.1016/s0008-6215(00)86114-5

Cited by 75 publications

(34 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At pH lower than 8 (4.5 and 6), no absorption bands were observed in the absorption spectra of ONC-Trp ((d) and (e)). This is mainly due to the instability of the EDAC at lower pH resulting in the instability of the esterified ONC during the fist step of the coupling reaction between ONC and amino acid (Danishefsky and Siskovic 1971;Rzayev and Hillmyer 2005). At pH higher than 11, the same result (no coupling) was obtained (spectrum f).…”

Section: Resultsmentioning

confidence: 87%

Spectroscopic characterization of oxidized nanocellulose grafted with fluorescent amino acids

Barazzouk

Daneault

2011

Cellulose

View full text Add to dashboard Cite

A hardwood bleached kraft pulp was oxidized by sodium hypochlorite using 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) and sodium bromide in water as catalysts to produce oxidized fibers. These oxidized fibers were mechanically disintegrated into oxidized nano-elements which were separated from the coarse components by centrifugation to obtain oxidized nanocellulose (ONC). The ONC was then coupled with fluorescent amino acids using a two step coupling procedure. First, the ONC was activated by N-ethyl-N 0 -(3-dimethylaminopropyl) carbodiimide hydrochloride, forming a stable active ester in the presence of N-hydroxysuccinimide. Second, the active ester was reacted with the amino groups on the amino acids, forming an amide bond between the ONC and amino acids. The products (ONC-amino acids) were characterized by transmission electron microscopy and by different spectroscopic techniques such as absorption, emission, FTIR and XPS.

show abstract

Section: Resultsmentioning

confidence: 87%

Spectroscopic characterization of oxidized nanocellulose grafted with fluorescent amino acids

Barazzouk

Daneault

2011

Cellulose

View full text Add to dashboard Cite

show abstract

“…Therefore, some chemical modificalogical tissues. This biomolecule has been used in tions 17 will be necessary to find more versatile medicine and cosmetics, mostly based not on the applications of HA. One of the promising modifiphysiological activities but on the physicochemications is introduction of crosslinking into HA cal properties.…”

Section: Introductionmentioning

confidence: 99%

Crosslinking of hyaluronic acid with glutaraldehyde

Tomihata

Ikada

1997

J. Polym. Sci. A Polym. Chem.

135

View full text Add to dashboard Cite

“…At pH lower than 7, no absorption bands were observed in the absorption spectra of ONC-Trp-Ps indicating that no Trp-Ps has been attached to ONC. This result was due to the instability of the coupling agent EDAC at lower pH leading to the instability of the esterified ONC during the fist step of the coupling reaction between ONC and Trp-Ps (Danishefsky and Siskovic 1971;Rzayev and Hillmyer 2005). At pH higher than 10, the same result (no coupling) was obtained.…”

Section: Absorption Spectramentioning

confidence: 90%

“…At pH higher than 10, the same result (no coupling) was obtained. In fact, Danishefsky and Siskovic (1971) have reported that at higher pH the coupling reaction becomes slower. This demonstrates that the grafting of ONC with Trp-Ps or other peptides is favorable at pHs between 7 and 10.…”

Section: Absorption Spectramentioning

confidence: 99%

Tryptophan-based peptides grafted onto oxidized nanocellulose

Barazzouk

Daneault

2011

Cellulose

View full text Add to dashboard Cite

Oxidized nanocellulose (ONC) have been synthesized and grafted with tryptophan-based peptides of varying lengths using a two step coupling method. The ONC was first activated by N-ethyl-N 0 -(3-dimethylaminopropyl) carbodiimide hydrochloride, forming a stable active ester in the presence of N-hydroxysuccinimide. Then, the active ester was reacted with the amino groups of the peptide forming an amide bond between ONC and peptide. Using this method, the intermolecular connection of Trp-based peptides (TrpPs) was avoided and uniform coupling of peptides on ONC was achieved. The coupling reaction was very fast in mild conditions and without alteration of the polysaccharide. The obtained products (ONC-Trp-Ps) were characterized by transmission electron microscopy and by different spectroscopic techniques.

show abstract

Conversion of carboxyl groups of mucopolysaccharides into amides of amino acid esters

Cited by 75 publications

References 19 publications

Spectroscopic characterization of oxidized nanocellulose grafted with fluorescent amino acids

Spectroscopic characterization of oxidized nanocellulose grafted with fluorescent amino acids

Crosslinking of hyaluronic acid with glutaraldehyde

Tryptophan-based peptides grafted onto oxidized nanocellulose

Contact Info

Product

Resources

About