N‐acylamino acids and peptides I. The synthesis of N‐feruloylamino acids

Pooter, H. De; Ali, Haider; Sumere, C. F. Van

doi:10.1002/bscb.19730820307

Cited by 9 publications

(2 citation statements)

References 16 publications

(7 reference statements)

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“…These compounds were synthesized through a three-step procedure. The first step was the formation of the amides 3 , 4 , and 5 by reacting ferulic ( 1a ) and caffeic ( 1b ) acids with the ethyl ester of glycine ( 2a ) or the dimethyl ester of glutamic acid ( 2b ) using a coupling reaction. ,,, The reaction was accomplished in the presence of EDC, TEA, and DMAP as catalysts, according to the scheme reported in Figure . Yields were higher for ferulic acid derivatives 3 and 4 (54 and 75%, respectively) than for the amide of caffeic acid (32%).…”

Section: Resultsmentioning

confidence: 99%

“…Several amides synthesized by coupling hydroxycinnamic acids with amino acids have been described, such as N -feruloyl-glycine, − N -caffeoyl-glycine, ,, and N -feruloyl-glutamate, but none shows surfactant activity. The aim of the present study was to synthesize new multifunctional molecules of natural origin to be used in cosmetics.…”

Section: Introductionmentioning

confidence: 99%

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New Multifunctional Surfactants from Natural Phenolic Acids

Centini

Rossato

Sega

et al. 2011

J. Agric. Food Chem.

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Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New Multifunctional Surfactants from Natural Phenolic Acids

Centini

Rossato

Sega

et al. 2011

J. Agric. Food Chem.

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N‐Acylamino acids and peptides VI. A Simple synthesis of N‐acylglycines of the benzoyl‐ and cinnamyl type

and

Sumere

1978

Bulletin des Soc Chimique

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L a b o r a t o r y o f P l a n t B i o c h e m i s t r y S t a t e U n i v e r s i t y o f G h e n t L e d e g a n c k s t r a a t , 3 5 , 6 -9 0 0 0 -G H E N T . BELGIUM Received 1 1 / 1 0 / 7 8 -Accepted 1 3 / 1 1 / 7 8 ABSTRACT -A v e r y s i m p l e a n d f a s t m e t h o d f o r t h e s y n t h e s i s o f N -a c y l a m i n o a c i d s a n d p e p t i d e s f r o m t h e b e n z o y l -a n d c i n n a m y l t y p e i s d e s c r i b e d . T h e m e t h o d i s b a s e d o n t h e u s e o f N -h y d r o x y s u c c i n i m i d e a s r e a g e n t ( a c t i v e e s t e r m e t h o d ) . The c h a r a c t e r i s t i c s a n d c h r o m a t o g r a p h i c p a r a m e t e r s o f some new b e n z o y l g l yc i n e s a r e g i v e n .

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N‐Acylamino Acids and Peptides. VII. Synthesis of Oxygen‐Sensitive N‐Acylglycines (N‐Caffeoylglycine, N‐Protocatechuoylglycine and N‐Galloylglycine) and a N‐Acyldipeptide (N‐Caffeoylglycyl‐L‐Phenylalanine)

Hanselaer

D'haenens

Martens

et al. 1983

Bulletin des Soc Chimique

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The synthesis of N-caffeoylglycine (6) , N-protocatechuoylglycine (16) , N-galloylglycine (El and N-caffeoylglycyl-L-phenylalanine (1) by means of the active ester method is described. IntrodbctionAs a result of studies of the natural occurrence in the plant world of N-acylamino acids and peptides of the benzoyl and cinnamoyl type, the synthesis of a variety of such compounds (reference substances) has become an interest of this laboratory. In the past different methods have been used for the synthesis of the pseudopeptide bond between the carboxylic function of a phenolic acid and an amino function of an amino acid or peptide. In this connection reference can be made to the acid-chloride method" '''5) , the dicyclohexylcarbodiimide (DCCD) method"), the mixed anhydride meth~d("~'~) and the active ester method(6).While the first three methods must be considered as being rather tedious, the active ester method, using N-hydroxysuccinimide as a reagent, is far more elegant. Indeed, the reaction with N-hydroxysuccinimide which was introduced by Anderson et alJ7) , can easily be effected.In addition, it is frequently possible to omit several of the usual protection and deprotection reactions while at the same time the yields are usually high(6). However, in the case of the oxygen sensitive N-caffeoylglycine (6) the above mentioned active ester method gave rise to poor yields ( 2 0 % over two steps) ( 6 ) . Even more difficulties were encountered when the Nhydroxysuccinimide method was employed for the preparation of N-caffeoylglycyl-L-phenylalanine (1).Moreover, the latter compound, which could not be crystallized was also not sufficiently pure.The employment of the other active esters such as p.nitrophenylesters and 2,4-dinitrophenylesters did not overcome the above difficulties(*).A possible reason for the poor results could be formation of undesired side products, which easily arise by oxidation of the oxygen-sensitive ortho-phenolic groups from the caffeoyl moieties. Similar or even greater difficulties were encountered with protocatechuic (8, and gallic acid ( 9 , . For this reason, the phenolic groups in caffeic, protocatechuic or gallic acid were first protected with ethylchloroformate to form 0-(ethoxycarbonyl) phenolic acids and the title compounds could then be prepared in higher yields by the active ester method using N-hydroxysuccinimide. SynthesisThe synthesis of the N-acylglycines and the N-acyldipeptide under discussion is shown in scheme 1.The phenolic acids, caffeic acid (I), protocatechuic acid (8) and gallic acid (9, were allowed to react with ethylchloroformate and sodium hydroxide to yield the corresponding -1029 -

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N‐acylamino acids and peptides I. The synthesis of N‐feruloylamino acids

Cited by 9 publications

References 16 publications

New Multifunctional Surfactants from Natural Phenolic Acids

New Multifunctional Surfactants from Natural Phenolic Acids

N‐Acylamino acids and peptides VI. A Simple synthesis of N‐acylglycines of the benzoyl‐ and cinnamyl type

N‐Acylamino Acids and Peptides. VII. Synthesis of Oxygen‐Sensitive N‐Acylglycines (N‐Caffeoylglycine, N‐Protocatechuoylglycine and N‐Galloylglycine) and a N‐Acyldipeptide (N‐Caffeoylglycyl‐L‐Phenylalanine)

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