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Topic: Carbodiimide

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	EDC (Site not responding. Last check: 2007-10-11)
		Carbodiimide catalyzes the formation of amide bonds between carboxylic acids or phosphates and amines by activating carboxyl or phosphate to form an O-urea derivative.
		Carbodiimide is often used in the synthesis of peptides as the water-soluble derivative EDC or as the organic soluble derivative, N,N'-dicyclohexyl-carbodiimide (DCC).
		The second step of the electrode modification includes the carbodiimide couplig of the PQQ carboxylic groups to the amino groups of the cystamine monolayer in the presence of EDC (Katz et al., 1994).
	chem.ch.huji.ac.il /~eugeniik/edc.htm (892 words)

	U.S. Patent: 5536816 - Process for producing amides using catalytic amounts of an N-hydroxy compound - July 16, 1996
		Carbodiimides are known in the art to function as dehydrating agents in organic reactions.
		In carrying out this reaction of a carboxylic acid with an amine to produce an amide, the amount of carbodiimide dehydrating agent is not critical as long as said carbodiimide dehydrating agent is present in sufficient amounts to facilitate such reaction by dehydration to yield an amide.
		It is generally preferred when said carbodiimide dehydrating agent is present in molar amounts equivalent to the molar amount of carboxylic acid present in the reaction mixture.
	www.everypatent.com /comp/pat5536816.html (3963 words)

	Fluoroaliphatic radical containing carbodiimides - Patent 4024178
		The carbodiimides consist essentially of from 1 to a plurality, preferably not over 20, of carbodiimide groups, terminal organic radicals free from isocyanate-reactive hydrogen atoms connected to carbodiimide and, when two or more carbodiimide groups are present, also polyvalent, preferably divalent, organic linking groups which are residues of a polyisocyanate between successive carbodiimide groups.
		Carbodiimides are conveniently obtained by condensation of isocyanates in the presence of suitable catalysts as described, for example, in the patents of Table 2 and by Campbell et al., J. Org.
		Carbodiimides are usually made from diisocyanates and monoisocyanates in an inert solvent such as methyl isobutyl ketone, conveniently at a concentration of about 40% of dissolved materials, to which is added about 1% of the weight of the materials of a phospholine oxide or other suitable catalyst.
	www.freepatentsonline.com /4024178.html (3592 words)

	Polyisocyanates which contain carbodiimide groups and which are stable in storage - Patent 4294719
		The present invention relates to stable equilibrium mixtures of carbodiimides, uretone imines and organic isocyanates and to stable solutions of carbodiimides and uretone imines in polyisocyanates which are free from carbodiimide groups.
		(A) an equilibrium mixture of the carbodiimide and uretone imines of tolylene diisocyanate, and
		(A) an equilibrium mixture of the carbodiimide and uretone imines of hexamethylene diisocyanate, and
	www.freepatentsonline.com /4294719.html (11889 words)

	U.S. Patent: 5126422 - Coating compositions and coated heat-resistant substrates prepared therefrom - June 30, 1992
		The equivalents of A are the sum of equivalents of blocked isocyanate groups, carbodiimide groups and uretoneimine groups, wherein the blocked isocyanate groups and carbodiimide groups are counted as monofunctional groups and the uretoneimine groups are counted as difunctional groups.
		The equivalents of B are the sum of the carboxyl and carboxylic acid anhydride equivalents of component b) and optionally d) and the hydroxyl equivalents of component c).
		Carbodiimide formation was catalyzed by the addition of 2.0 g of a commercial mixture of 1-methyl-1-phospha-2-cyclopent-1-oxide and 1-methyl-1-phospha-3-cyclopent-1-oxide at 60.degree.
	www.everypatent.com /comp/pat5126422.html (3330 words)

	Studies on cyclic carbodiimides
		A comment about the structure of cyclic bis(carbodiimides): due to the chirality of cumulenes, each carbodiimide fragment exists as a mixture of R and S enantiomers, thus bis(carbodiimides) could exist as d,l or meso isomers.
		Furthermore, the three-dimensional structure could reveal whether the relative disposition of the carbodiimide fragments is favourable to the [2+2] cycloaddition.
		X-ray difraction analysis showed the diazetidine 6 as only one of the two possible isomers(6a and 6b), the one with an inversion centre, 6a, taking into account the pyramidalized nature of the diazetidine nitrogen atoms.
	www.ch.ic.ac.uk /ectoc/echet96/papers/073 (899 words)

	Patent 6,013,679 (Site not responding. Last check: 2007-10-11)
		This is chemically different from the HA amide product made by the carbodiimide activation of HA followed by a nucleophilic attack by a nucleophile such as an amine.
		Preferably, the HA solution has a concentration of between about 0.1% and about 5%; the acid includes hydrochloric acid; the carbodiimide is either a soluble monocarbodiimide or biscarbodiimide; and the molar equivalent ratio of the carbodiimide to the HA is equal to or greater than 5%.
		A method for preparing a water-insoluble biocompatible gel, comprising reacting hyaluronic acid, or a salt thereof, with a carbodiimide to form a water insoluble gel in the absence of a nucleophile and a polyanionic polysaccharide other than the hyaluronic acid of the reaction.
	www.pharmcast.com /Patents/011100OG/6013679_hyaluronic011100.htm (970 words)

	Easy and versatile conversion of the thiazetidinone into carbodiimide or isourea derivatives
		A carbodiimide could be obtained initially by hydrolysis of N,N'-disubstituted carbamido chlorides as observed by Eilingsfeld, Seefelder, and Weidinger<60AG(E)48> (Scheme 2) and then be converted to the isourea by treatment with an appropriate alcohol and catalyst
		A mixture of the starting material 4 and carbodiimide 6 was obtained when 4 was heated to reflux in dichloromethane containing one and a half equivalents of ethanol.
		Synthesis of carbodiimide 6 was also performed through the more classical desulfurization method using lead oxide<53LA77> in refluxing acetone.
	www.ch.ic.ac.uk /ectoc/echet96/papers/019 (718 words)

	[Preparation of immunoenzyme conjugates of beta-lactamase from Bacillus licheniformis 749/c and horseradish peroxidase ...
		By using three different linkage methods with carbodiimide, glutaraldehyde and periodite, immunoenzyme conjugates of beta-lactamase from Bacillus licheniformis 749/c and horse radish peroxidase with human antibodies to HIV-1 were prepared.
		It was shown that the conjugates prepared by the carbodiimide linkage method had the highest titer, the beta-lactamase conjugate being superior by its titer to the respective peroxidase conjugate.
		In the lyophilized state the conjugates prepared with the carbodiimide linkage method were stable.
	www.aegis.com /aidsline/1992/jun/M9260929.html (356 words)

	Synthesis and Reactivity of Iminophosphorane Catalysts
		The focus of our research for the past semester has been on the synthesis of iminophosphoranes.
		It is known that these iminophosphorane compounds can exist in a monomer/dimer equilibrium (Scheme 1).
		The size differences in these elements and their differences in electron-withdrawing ability are expected to affect the dimerization and also the propensity of these species to react with imine or carbodiimide substrates.
	www.sis.pitt.edu /~lmann/project3/badeyiga_0101.htm (326 words)

	NTP: Executive Summary Diisopropylcarbodiimide: Carcinogenic Activity
		Carbodiimides were nominated for toxicity testing to the NTP but testing was deferred pending response from the submitter for a specific carbodiimide of concern (National Toxicology Program, 1991).
		However, RTECS (1991) cites one study on the oral reproductive toxicity of carbodiimide in rats.
		A dose of 2450 mg/kg caused pre-implantation mortality; 1750 mg/kg caused paternal effects (testes, epididymis, sperm duct, prostate, seminal vesicle, Cowper's gland, and accessory glands); 208 mg/kg effected post-implantation mortality and the live birth index; 2600 mg/kg also affected newborns (live birth index, growth statistics, and delayed effects).
	ntp-server.niehs.nih.gov /index.cfm?objectid=03DDFA29-C6CC-847C-41EECB29A0880437 (669 words)

	OEL: UROP - Synthesis and Reactivity of Iminophosphorane Catalysts - Bunmi Adeyiga - College of Arts and Sciences, ... (Site not responding. Last check: 2007-10-11)
		The size differences in these elements and their differences in electron-withdrawing ability are expected to affect the dimerization and also the propensity of these species to react with imine or carbodiimide substrates.
		The new chloro-derivative reacted with diisopropyl carbodiimide, forming phosphetidine compound 2 (Scheme 3).
		We are currently preparing the bromo-derivative and plan to study the relative reactivities of all of the derivatives with unsaturated substrates containing C=N bonds.
	www.pitt.edu /~urop/research/badeyiga_0101.htm (343 words)

	Peptide synthesis (Site not responding. Last check: 2007-10-11)
		Watts and co-workers have recently demonstrated multistep synthesis of peptides in a micro reactor [9].
		The authors evaluated the reactor using a carbodiimide coupling reaction of Fmoc-beta-alanine with the amine to give the dipeptide in up to 93% conversion (Fig.
		The authors also demonstrated that the dipeptide could be prepared from pre-activated carboxylic acids [9].
	www.arches.uga.edu /~asmehta/peptide.html (116 words)

	Effects of Chemical Modifications on Physicochemical and Cake-Baking Properties of Egg White
		The extent of succinylation was determined from the free amino contents by the method of Concon (1975) using dinitrobenzene sulfonate (DNBS).
		The carboxyl groups in EWS were modified by the carbodiimide-promoted amide formation (Hoare and Koshland, 1967), using 10 mM of a water soluble carbodiimide, EDC, and glycine methyl ester (as a nucleophile) at two different concentrations (20 and 50 mM respectively).
		The extent of modification was determined from amino acid analysis by measuring the increase in glycine content of the protein after modification (Hoare and Koshland, 1967).
	albumen.stanford.edu /library/c20/ma1986.html (3969 words)

	Theoretical Study of the Quadrupolarity of Carbodiimide
		The quadrupolarity of carbodiimide, HN=C=NH, has been studied in comparison to carbon dioxide.
		of carbodiimide falls between -16 and -18 DÅ.
		values of carbodiimide are close to zero and only the off-diagonal quadrupole moment element
	pubs.acs.org /cgi-bin/abstract.cgi/jpcafh/2002/106/i34/abs/jp020553r.html (255 words)

	a letterhead ccr memo (Site not responding. Last check: 2007-10-11)
		This method involves the use of water-soluble carbodiimides to activate carboxyl groups on peptides and proteins (Asp and Glu residues).
		The resultant moieties are quite antigenic and are specific for the type of carbodiimide used for formation of the conjugate.
		For this reason, it is not a good idea to screen serum using a conjugate formed using the same water soluble carbodiimide.
	web.mit.edu /biopolymers/www/peptide_synthesis.html (2894 words)

	Peptide-Carrier Protein Conjugation - # AG086
		Client supplied peptide (5 milligrams) is conjugated to keyhole limpet hemocyanin (KLH) or BSA using either maleimide or carbodiimide coupling chemistry.
		The carbodiimide method will work for most other peptides but can link internal to the peptide, possibly disrupting the antigenic structure of the resulting immunogen The conjugate is purified away from unreacted peptide and supplied frozen.
		Process efficiency is affected by a number of factors, including the specific sequence of the peptide supplied for the conjugation and the method of conjugation (maleimide or carbodiimide).
	www.virusys.com /Services/ag086.html (233 words)

	n of Extrasynovial Tendon by Carbodiimide Derivatized Hyaluronic Acid (Cd-Ha) Gelatin for Flexor Tendon Graft
		In addition to anatomic and biological differences between intrasynovial and extrasynovial tendons, recent studies have shown a significant difference in friction, with the extrasynovial tendon having the rougher gliding surface.
		The purpose of this study was to test the hypothesis that carbodiimide derivatized HA gelatin (cd-HA-G) improves the gliding of extrasynovial tendon grafts within short term (one week) in vivo using canine model.
		Work of flexion (WOF), gliding resistance, and quantification of the HA binding to the tendon surface was analyzed.
	mayoresearch.mayo.edu /mayo/research/biomechanics/hand12.cfm (269 words)

	HETEROCUMULENES AS THE DIENIC COMPONENT IN [4+2] CYCLOADDITIONS
		reas the formation of pyrido[2,3-b]indoles 4 involves a [4+2] cycloaddition whereby the unsaturated carbodiimide has functioned as a 2-azadiene (using a cumulative C=N double bond and the styryl C=C double bond), and the C=C double bond of the ortho-vinyl substituent has taken the role of the dienophile.
		This work showed for the first time an intramolecular [4+2] cycloaddition involving a carbodiimide as the dienic component.
		Our first attempt was the reaction of iminophosphorane 11 with 4-methylphenylisocyanate to generate N-(2-allyl)phenyl-N’-(4-methyl)phenyl carbodiimide 7, which by thermal treatment unexpectedly produced the quinoline 13.
	www.mdpi.org /ecsoc/ecsoc-5/Papers/a0017/a0017.htm (672 words)

	Attachment of oligonucleotide probes to poly carbodiimide-coated glass for microarray applications -- Kimura et al. 32 ...
		Carbodiimides are reactive functional groups used in DNA modification
		is that the carbon of a carbodiimide group may react at position
		Metz,D.H. and Brown,G.L. (1969) The investigation of nucleic acid secondary structure by means of chemical modification with a carbodiimide reagent.
	nar.oxfordjournals.org /cgi/content/full/32/7/e68 (4234 words)

	Immunocytochemical Localization of Histamine in Enterochromaffin-like (ECL) Cells in Rat Oxyntic Mucosa: A Transmission ...
		Nissinen MJ, Panula P (1993) Histamine-storing cells in the oxyntic mucosa of the rat stomach: a transmission electron microscopic study employing fixation with carbodiimide.
		Nissinen MJ, Panula P (1995) Developmental patterns of histamine-like immunoreactivity in the mouse.
		Panula P, Happola O, Airaksinen MS, Auvinen S, Virkamaki A (1988) Carbodiimide as a tissue fixative in histamine immunohistochemistry and its application in developmental neurology.
	www.jhc.org /cgi/content/full/47/8/1031 (3483 words)

	[No title]
		or excessive heating of isopropyl isocyanate from 100°C to 250°C under anhydrous conditions to condense the carbodiimide with elimination of carbon dioxide.
		A number of catalysts are effective in accelerating this reaction to the extent of making it a practical synthesis for this symmetrical carbodiimide.
		Like most carbodiimides, DIC has also been used in dehydration reactions for conjugated alkadienoic acid and anhydride preparations.
	ntp-server.niehs.nih.gov /ntpweb/printFriendly.cfm?objectid=03DDFDF1-98E8-2FD6-5EB1FEF08A167321 (711 words)

	Activation and coupling
		Many of these are based on the chemistry of the carbodiimide group where the neighboring C=N bonds are susceptible to nucleophilic attack by the carboxyl group forming an isourea with dehydration be favored by the formation of a highly stable urea (Figure).
		There is a risk of the amine nucleophile itself reacting with the carbodiimide resulting In the formation of an undesired guanidine but this reaction is sufficiently slow to be unimportant in the conditions conventionally used for peptide synthesis.
		It does, however, prove to have a low degree of solubility in the presence of other dissolved material and is remarkably persistent in its contamination of the coupling product.
	www.vuw.ac.nz /staff/paul_teesdale-spittle/peptide-synthesis/pep-syn-files/activation-coupling.htm (827 words)

	Synthesis of ferrocenyl carbodiimide as a novel ferrocenyl reagent of single stranded DNA -- Mukumoto et al. 48 (1): ...
		Synthesis of ferrocenyl carbodiimide as a novel ferrocenyl reagent of single stranded DNA -- Mukumoto et al.
		Articles by Mukumoto, K. Articles by Takenaka, S. Synthesis of ferrocenyl carbodiimide as a novel ferrocenyl reagent of single stranded DNA
		Ferrocenyl carbodiimide (FcCDI) was newly synthesized as a ferrocenylation
	nass.oxfordjournals.org /cgi/content/abstract/48/1/251 (163 words)

	Histamine Compartments of the Drosophila Brain With an Estimate of the Quantum Content at the Photoreceptor Synapse -- ...
		carbodiimide, heads were cryoprotected in 25% sucrose and cut
		Nässel DR, Holmqvist MH, Hardie RC, Håkanson R, and Sundler F. Histamine-like immunoreactivity in photoreceptors of the compound eyes and ocelli of the flies Calliphora eythrocephala and Musca domestica.
		Panula P, Häppölä O, Airaksinen MS, Auvinen S, and Virkamäki A. Carbodiimide as a tissue fixative in histamine immunohistochemistry and its application in developmental neurobiology.
	jn.physiology.org /cgi/content/full/93/3/1611 (5170 words)

	abstract79 (Site not responding. Last check: 2007-10-11)
		Pyrroloquinoline quinone (PQQ) was immobilized on gold electrodes by prior adsorption of the polyamines polyethylenimine, and triethylene tetraamine, followed by carbodiimide coupling of PQQ to the surface-adsorbed amine groups.
		The stability and electrochemical behavior of the electrodes, in which the amino-containing linker molecule is adsorbed on the electrode surface, were compared with those of electrodes prepared by carbodiimide coupling of PQQ to a cystamine monolayer, in which the sulfur-containing linker molecule is associated with the gold surface.
		The electrodes prepared using adsorbed polyethylenimine showed comparable stability to those based on a cystamine monolayer, but reveal enhanced stability to application of negative potentials (< -1.1 V).
	chem.ch.huji.ac.il /~eugeniik/abstract79.htm (135 words)

	INABIS '98 - Tethering of Oligo DNA Probes to Polyethylene-co-acrylic Acid — a Superior Support For Nucleic Acid ...
		The film has relatively few carboxylate functions on its surface, but the density of these may be increased by treatment with strong base above the glass transition temperature or by treatment with thionyl chloride and subsequent hydrolysis.
		DNA oligos synthesized with C12-alkyl amino tails may be exclusively end-tethered to PEAA using either conventional carbodiimide chemistry or unconventional subsurface amide formation if the acid chloride of PEAA is used.
		The carbodiimide reaction takes place at a pH well below the pKa of the oligo's amine tail because of rapid amine deprotonation kinetics.
	www.mcmaster.ca /inabis98/cellbio/zhang0791 (295 words)

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