Die Hydroxylaminolyse <i>N</i>‐substituierter Phthalimide, ein Verfahren zur Darstellung von Peptiden und <i>N</i>‐Hydroxy‐peptiden

Neunhoeffer, Otto; Lehmann, Günter; Haberer, Dieter; Steinle, Georg

doi:10.1002/jlac.19687120125

Cited by 18 publications

(2 citation statements)

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“…Rapid methylaminolysis of such a compound, as in the dephthaloylation described above, is therefore consistent with these properties. Hydrazinolysis (32) is the generally accepted procedure for removal of the phthalimido group in the Gabriel synthesis (1) and in peptide synthesis (33), although base-catalyzed hydroxylaminolysis has been recommended recently as an alternative (34). The present methylamine procedure ought to provide a useful adjunct to these other methods because of its simplicity and the ease of removal of excess amine from reaction mixtures.…”

Section: " Cood C02dmentioning

confidence: 99%

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Wolfe¹,

Hasan²

1970

Can. J. Chem.

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A reexamination of the literature on inter and intramolecular reactions of amines with N-substituted phthalimides has led to the demonstration that methylamine is a convenient reagent for removal of a phthaloyl protecting group from nitrogen at room temperature. Application of this procedure (first described in 1896) to the Gabriel synthesis of primary amines and to peptide synthesis is recommended. The simplicity of the reaction is a consequence of the consecutive occurrence of two unexpectedly rapid processes: (1) methylaminolysis of one of the imide bonds; (2) intramolecular catalysis, by an N-methylamido group, of the hydrolysis or aminolysis of an adjacent phthalamido linkage.Some unsuccessful attempts to prepare 2-aminoethylphthalimide are also described.

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Section: " Cood C02dmentioning

confidence: 99%

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Wolfe¹,

Hasan²

1970

Can. J. Chem.

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“…In addition to hydrazine, 10 • 19 • 20 phenylhydrazine, 14 • 21 and hydroxylamine 22 have been applied for the same purpose. First, treatment of 5a-f with hydrazine hydrate gave a mixture of the desired ester (6a-f) and its phthaloylhydrazinium salts.…”

Section: S' Imentioning

confidence: 99%

Synthesis and Estimation of Poly[γ-(4-alkoxyphenyl)-benzyl-L-glutamate]s

Hanabusa

Tanaka

Koyama

et al. 1988

Polym J

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ABSTRACT:The synthesis and thermal properties of new thermo tropic liquid crystalline (LC) poly[y-4-( 4' -alkoxyphenyl)benzyl-L-glutamate]s (8) are described. y-4-( 4' -Alkoxyphenyl)benzyl-Lglutamates (6a-f) are prepared by the addition of 4-alkoxy-4' -hydroxymethylbiphenyl (3a-f) to N-phthaloyl-L-glutamic anhydride (4), followed by removal of the N-protecting group. 8a-f are synthesized by the polymerization of y-4-(4' -alkoxyphenyl)benzyl-L-glutamate-N-carboxyanhydrides (7a-f), which are prepared by treatment of 6a-f with phosgene. Although 8a--c do not show transition peaks in DSC heating curves, 8d-f show two endothermic transition peaks. Viewing on the hot stage with a polarizing microscope suggests that the first transition is due to the transition from the crystalline state to the I st LC state and the second one is attributed to the transition from the I st LC state to the 2nd LC state. Therefore, the long alkyl segment with more than a certain carbon number as the side chain of 8 is essential for the appearance of thermo tropic LC state.KEY WORDS Polypeptide / Poly(y-benzyl-L-glutamate) / Thermotropic Liquid Crystalline Polymer / During the past years, numerous polymers have been reported to form thermotropic liquid crystalline (LC) states. These thermotropic LC polymers-can be classified structurally into three types. Two of these types are well-known as main-chain and side-chain thermotropic LC polymers. 1 In the former, the mesogenic groups form the backbones of molecular chains; whereas in the latter, the mesogenic segments link to a polymer backbone as pendants in side chains. A third type 2 is relatively new and represented by polymers forming mesogenic rods surrounded by long hydrocarbon side chains. The transition from crystal to LC for the third type polymer seems to occur by melting of long hydrocarbon chains on heating and subsequently acting as solvents in the similar manner to the lyotropic LC state. 3 Therefore, the structures of polymers of the third type are closely relating to those of lyotropic LC polymers. For example, cellulose derivatives by Tseng et al., 4 • 5 poly(yalkyl glutamate)s by Watanabe et al. 2 • 6 and poly(y-alkoxybenzyl-L-glutamate)s by us 3 • 7 are thought to be thermotropic LC polymers of the third type.In this paper, we report the sythesis and thermotropic LC behavior of new poly [y-(4-861

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Zur Acylierung von prim. Aminen durch Phthalimide. 1. Mitt.

Endres

1972

Archiv der Pharmazie

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Die Hydroxylaminolyse N‐substituierter Phthalimide, ein Verfahren zur Darstellung von Peptiden und N‐Hydroxy‐peptiden

Cited by 18 publications

References 10 publications

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Five-membered rings. II. Inter and intramolecular reactions of simple amines with N-substituted phthalimides. Methylamine as a reagent for removal of a phthaloyl group from nitrogen

Synthesis and Estimation of Poly[γ-(4-alkoxyphenyl)-benzyl-L-glutamate]s

Zur Acylierung von prim. Aminen durch Phthalimide. 1. Mitt.

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