Succinimides hydroxy

Further versatihty was added to the range of substituents available for introduction into the 6a-position by use of the 6a(succinimido-oxy) derivative (18) prepared by treatment of the 6a-(methylthio) derivative (17) with A/-hydroxy-succinimide and silver(I) acetate in dimethylformamide in virtually quantitative yield. In this way the 6a-cyanopeniciILin (19, X = CN), 6a-viny1penici11in (19, X = CH=CH2) and 6a-pheny1penici11in (19, X = C H ) could be prepared in high yield (43). 

Succinimides — see also Pyrrolidine-2,5-diones as anticonvulsants, I, 166 synthesis, 4, 120 Succinimides, N-hydroxy-polymerization, I, 271-272 Sudoxicam... 

The Bsmoc derivative is formed from the chloroformate or the A -hydroxy-succinimide ester. It is cleaved rapidly by a Michael addition with tris(2-aminoethyl)amine at a rate that leaves Fmoc derivatives intact. More hindered bases, such as A -methylcyclohexylamine or diisopropylamine, do not react with the Bsmoc group, but do cleave the Fmoc group, illustrating the importance of steric effects in additions to Michael acceptors. 

The values of the 1-hydroxy moiety of (5)-(- -)-iVb-acetyl- 1-hydroxytrypto-phan methyl ester (32), methyl l-hydroxyindole-3-butylate (33), iVb-methoxy-carbonyl-l-hydroxytryptamine (34), 1-hydroxymelatonm (19), l-hydroxy-6-nitroindole (35), and l-hydroxy-5-nitroindole (36) are determined to be 9.8, 8.4, 8.2, 8.1, 6.9, and 6.8, respectively (Fig. 2) (2000H1881). Thus, 1-hydroxyindoles are weak acids, stronger than phenol and weaker than succinimide. Therefore,... 

I n the above procedure, the use of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride in place of 4-hydroxy-1,5-naphthyridine-3-carboxyllc acid N-succinimide ester can also afford the same objective compound as above. The use of sodium thio-n-propoxide in place of sodium thiophenoxide can also give the objective compound in the form of the sodium salt. 

PGIP, purified fi om P.vulgaris hypocotyls [11], was immobilized to the sensor ch via amine coupling. A continuous flow of HBS buffer (5 pl/min) was mantained over the sensor surface. The carboxylated dextran matrix of the sensor surface was first activated by a 6-min injection of a mixture of N-hydroxy-succinimide and N-ethyl-N - (3-diethylaminopropyl) carbodiimide, followed by a 7-min injection of PGIP (lOng/pl in 10 mM acetate, pH 5.0). Hie immobilization procedure was con leted by a 7-min injection of 1 M ethanolamine hydrochloride to block the remaining ester groups. 

The most widely applied principle is haptenylation of amino groups via A-hydroxy succinimide esters (NHS-ES). For convenient protein-labeling procedures,... 

Label amino function in DNA probe with N-hydroxy succinimide derivatives of acridinium esters. 

Radford GM, Ariatti M, Hawtrey AO. Cholesterylsuccinyl-N-hydroxy-succinimide as a cross-linking agent for the attachment of protein to liposomes. Biochem Pharmacol 1991 41 307. 

Fig. 8 Examples of homobifimctional crosslinkers a bisimidate and b N-hydroxy-succinimide ester...

The Beckmann rearrangement of ketoximes with triphenylphosphine and iV-chloro-succinimide occurs at room temperature almost instantaneously and their corresponding secondary amides are obtained in high yields (equation 83). The triphenylphosphine 271 is activated by the iV-chlorosuccinimide 270 affording the salt 272, which is attacked by the iV-hydroxy group of the oxime 217 forming the intermediate 273. 

Slepnev et al. [313] presented a simple method for protein radio-labeling with Bolten-Hunter reagent (iV-hydroxy succinimide ester of 3-(p-hydroxy di-iodophenyl)) propionic acid) in AOT/octane-RMs using mouse IgG, human transferrin, protein A, and a2-interferon as labeling examples. The yield of radio-labeling in RMs was found to be higher than that achieved in homogeneous aqueous solution. 

To a solution of diacetone-a-D-glucose [Eq. (9)] 28 (2.60 g, 10 mmol), jV-hydroxy-succinimide (NHS, 0.115 g, 1 mmol), and dry pyridine (2.43 mL, 30 mmol) in THF (50 mL) was added 4-fluorophenyl chlorothionoformate (3.81 g, 20 mmol) dropwise at room temperature under argon. The solution was stirred for an additional 2 h. The organic layer was washed with 1 M HC1, saturated NaHCOj, brine, and dried over anhydrous MgS04. After evaporation of the solvent under reduced pressure, the thionocarbonale by-product was precipitated with hexanes. After filtration and evaporation, the crude product was purified by column chromatography over silica gel (eluting with n-hexane-CHjClj, 7 3) to afford 3.13 g (76%) of the thionocarbonate 32 mp 82°-83°C (EtOH-H20) [a], —33° (c 1, CHClj). 

Maleimido groups are introduced into AChE by reaction of their primary amino groups with the jV-hydroxy-succinimide moiety of SMCC m neutral medium. This reaction is very similar to that used for incorporation of biotin molecules into proteins Prior to this reaction, the enzyme is treated with / /-ethyl maleimide in order to block any thiol groups. Finally, SMCC-AChE is purified by molecular sieve chromatography on a Biogel A 1.5 m column. 

Boc amino acid thioesters 7 used in Boc-SPPS are prepared by reaction of Boc amino acid active esters such as the 4-nitrophenyl ester (ONp) or succinimide ester 6 (OSu) with thiols containing a carboxy group that can link to a resin (Scheme 3, Table 2). 1314 Amino acid thioesters 7 can also be prepared by reaction of Boc amino thiol acids 8 with a chloro, bromo, or hydroxy compound that also contains a carboxy group (Scheme 3, Table 2). 1516 ... 

Di- and oligo-peptides with a terminalo-aminophosphonous acid residue have been prepared by coupling with N-hydroxy succinimide esters of N-benzyloxycarbonylamino acids or peptides. 

Hydroxy-l,5-naphthyridine-3-carboxylic acid N-succinimide ester Sodium bicarbonate Sodium thiophenoxide Triethylamine... 

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