THE USE OF HYDROGEN BROMIDE IN ACETIC ACID FOR THE REMOVAL OF CARBOBENZOXY GROUPS AND BENZYL ESTERS OF PEPTIDE DERIVATIVES<sup>1</sup>

Ben‐Ishai, D.

doi:10.1021/jo01366a011

Cited by 98 publications

(23 citation statements)

References 6 publications

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“…Die Z-Gruppe kann hydrogenolytisch [6] beseitigt, die erheblich säureempfindlichere BOC-Gruppe mit kalter was serfreier TFA [7] abgespalten werden. Die geschützten Lipoornithine 1, 3, 5, 7 werden durch Behandlung mit Brom wasserstoff in Eis essig [8] bzw. Hydrogenolyse [6] deblockiert und als Hydrobrom ide bzw.…”

Section: Synthesenunclassified

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Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Kellner

Liefländer

1991

Zeitschrift Für Naturforschung B

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Synthetic Lipo Amino Acids, Synthetic Lipopeptides, M onolayer, Surface Pressure, Area IsothermsLipo amino acids and a-as well as ^-connected lipodipeptides o f ornithine were synthesized. The lipid portion was introduced to the amino group by acylating with hexadecanoyl chloride and to the carboxylic group by amidating with hexadecylamine or octadecylamine, respective ly. Due to their amphiphilic properties these com pounds were measured in a L A N G M U IRtrough and thus their ability to form m onom olecular films was examined. Dates from the sur face pressure -area isotherms are listed in the follow ing com position.

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Section: Synthesenunclassified

“…Zur Abspaltung der Z-und BOC-Schutzgruppen a) mit Bromwasserstoff in Eisessig [8] Die geschützte Verbindung wird in 33-proz. Bromwasserstoff in Eisessig gelöst und 2 h bei R.T. gerührt (5 -1 0 ml pro Gramm).…”

Section: Allgemeine Vorschrift(en)unclassified

Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Kellner

Liefländer

1991

Zeitschrift Für Naturforschung B

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“…by weak base or reduction. HBrjAcOH [41][42][43], liquid HF [27]) for final deprotection (see ref. HCl in organic solvents, trifluoroacetic acid with or without diluents, ref.…”

Section: Acohe]mentioning

confidence: 99%

Protected Amino Acids in Peptide Synthesis

Meienhofer¹

1985

Chemistry and Biochemistry of the Amino Acids

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“…m.p. 84" [4]). Labeled carbobenzoxyphenylalanine (3.4 g) was dissolved in 20 ml of tetrahydrofuran and cooled in an ice-salt bath; 1-4 ml of triethylarnine and 1 *O ml of ethyl chloroformate were added and the mixture shaken during 15 min.…”

Section: Preparation Of Phenylalanyl-3 14c-glycine-214cmentioning

confidence: 99%

“…The precipitate of labeled carbobenzoxyphenylalanylglycine was recrystallized from dioxane and petroleum ether. Labeled carbobenzoxyphenylalanylglycine (2 g) was suspended in 25 ml of warm nitromethane and hydrogen bromide gas passed in for 5 min [4]. The mixture was allowed to stand for 1 hr, filtered, and the precipitate washed with ether.…”

Section: Preparation Of Phenylalanyl-3 14c-glycine-214cmentioning

confidence: 99%

Photolysis and Radiolysis of Phenyl‐alanylglycine

Wheeler

Julian

Ribot

1970

Photochem & Photobiology

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The Photolysis of glycine and alanine containing peptides in oxygenated solution has been shown to result in the formation of glyoxylic and pyruvic acids, through oxidative cleavage of the peptide bond[1]. The same products were formed in the radiolysis of such peptides in the presence of oxygen[2]. In a peptide containing aromatic amino‐acids the absorption of light results in the excitation of the aromatic ring and it has been postulated[3] that energy is transferred to the peptide bond, resulting in the formation of a radical on the carbon atom adjacent to the peptide bond. Radiolysis, however, involves the attack of hydroxyl radicals and other reactive species formed in the absorption of radiation by water[2]. This study compares the behavior of phenylalanylglycine to photolysis and radiolysis in aerated aqueous solution in relation to a possible energy transfer in photolysis.

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THE USE OF HYDROGEN BROMIDE IN ACETIC ACID FOR THE REMOVAL OF CARBOBENZOXY GROUPS AND BENZYL ESTERS OF PEPTIDE DERIVATIVES¹

Cited by 98 publications

References 6 publications

Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Protected Amino Acids in Peptide Synthesis

Photolysis and Radiolysis of Phenyl‐alanylglycine

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THE USE OF HYDROGEN BROMIDE IN ACETIC ACID FOR THE REMOVAL OF CARBOBENZOXY GROUPS AND BENZYL ESTERS OF PEPTIDE DERIVATIVES1

Cited by 98 publications

References 6 publications

Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Synthese und Eigenschaften von Lipoaminosäuren und Lipodipeptiden des Ornithins / Synthesis and Properties of Lipo Amino Acids and Lipodipeptides of Ornithine

Protected Amino Acids in Peptide Synthesis

Photolysis and Radiolysis of Phenyl‐alanylglycine

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Product

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THE USE OF HYDROGEN BROMIDE IN ACETIC ACID FOR THE REMOVAL OF CARBOBENZOXY GROUPS AND BENZYL ESTERS OF PEPTIDE DERIVATIVES¹