Some N-acyl-D-amino acid derivatives having antibotulinal properties

1987 ◽  
Vol 33 (7) ◽  
pp. 577-582 ◽  
Author(s):  
A. Paquet ◽  
K. Rayman
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Aspartic Acid ◽  
Sodium Nitrite ◽  
Amino Acid Derivatives ◽  
Ester Method ◽  
Succinimidyl Ester ◽  
High Yields ◽  
Derivatives Of ◽  
Acyl Derivatives

Several N-acyl derivatives of D-tryptophan, D-alanine, D-methionine, D-valine, and D-aspartic acid were synthesized in high yields using the succinimidyl ester method and examined for their antibotulinal properties. In conjunction with 60 ppm of sodium nitrite, sorbyl-D-tryptophan, sorbyl-D-alanine, myristoyl-D-aspartic acid, and glycyl-D-alanine were highly inhibitory. In the absence of sodium nitrite, the N-acyl derivatives of the D-amino acids were not inhibitory. On its own, 60 ppm of sodium nitrite was only slightly inhibitory. Sorbyl-L-tryptophan and sorbyl-L-alanine had no effect in the presence or absence of 60 ppm of sodium nitrite.

Darstellung und Charakterisierung von Triphenylbleiderivaten einiger Aminosäuren/Preparation and Characterization of Triphenyllead Derivatives of Some Amino Acids

1981 ◽  
Vol 36 (8) ◽  
pp. 945-948 ◽  
Author(s):  
Gerd Roge ◽  
Friedo Huber
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Aspartic Acid ◽  
Acid Ph ◽  
Carboxylate Groups ◽  
Inferred Ph ◽  
Derivatives Of

Abstract Triphenyllead derivatives Ph3PbL (HL = glycine, alanine, phenylalanine) and (Ph3Pb)2L′ (H2L′ = aspartic acid) have been prepared from Ph3PbOH and the appropriate amino acid. PH3Pb-leucinate has been synthesized from Ph3PbCl and Tl(I)-leucinate. From IR data structural proposals are inferred: Ph3Pb-glycinate is polymeric through monodentate carboxylate and coordinating NH2; Ph3Pb-alaninate, -phenylalaninate, and -leucinate contain bidentate carboxylate and non-coordinating NH2 groups and are probably monomeric. For (Ph3Pb)2-aspartate and (Me3Sn)2-aspartate a structure with coordinating NH2 and mono-and bidentate carboxylate groups is proposed.

ChemInform Abstract: AMINO ACID DERIVATIVES OF PHENYLALKYLAMINE PART 3, ACYLATION OF BETA-PHENYLETHYLAMINE DERIVATIVES WITH ALPHA-AMINO ACIDS

1975 ◽  
Vol 6 (26) ◽  
pp. no-no
Author(s):  
I. D. KISELEVA ◽  
N. S. VOLODARSKAYA ◽  
D. N. MASLIN ◽  
YU. A. DAVIDOVICH ◽  
S. V. ROGOZHIN ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Derivatives Of

scholarly journals Novel Nucleoside Phosphoramidates as Inhibitors of HIV: Studies on the Stereochemical Requirements of the Phosphoramidate Amino Acid

1996 ◽  
Vol 7 (4) ◽  
pp. 184-188 ◽  
Author(s):  
C. McGuigan ◽  
A. Salgado ◽  
C. Yarnold ◽  
T.Y. Harries ◽  
E. De Clercq ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Antiviral Activity ◽  
Antiviral Effect ◽  
Amino Acid Derivatives ◽  
Free Nucleotides ◽  
Nucleoside Phosphoramidates ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Marked Dependence

Novel phosphoramidate derivatives of the anti-HIV nucleoside analogue d4T were designed to act as labile membrane-soluble prodrugs of the bio-active free nucleotide d4TMP. We herein reveal the very marked dependence of the antiviral activity of these phosphoramidates upon the stereochemistry of the amino acid attached to the phosphate centre; with a strong preference for the L-stereochemistry. These phosphate triesters were shown to liberate amino acid derivatives of the nucleotide intracellularly. These novel analogues, typified by alaninyl d4T monophosphate, may act as intracellular sources of the free nucleotides. The alaninyl d4T adducts themselves exert an antiviral effect when administered extracellularly, but again with clear distinctions between the L- and D-series. This evidence indicates that extracellularly administered blocked triesters derived from L-amino acids can generate d4TMP intracellularly, by a new pathway which is highly dependent on the amino acid stereochemistry.

Piezoactive amino acid derivatives containing fragments of planar-chiral ortho-carboranes

2018 ◽  
Vol 6 (32) ◽  
pp. 8638-8645 ◽  
Author(s):  
Dmitry A. Gruzdev ◽  
Alla S. Nuraeva ◽  
Pavel A. Slepukhin ◽  
Galina L. Levit ◽  
Pavel S. Zelenovskiy ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Derivatives ◽  
Piezoelectric Activity ◽  
Derivatives Of

Compounds possessing a high piezoelectric activity have been found among enantio pure ortho-carboranyl derivatives of amino acids.

Papain-catalyzed synthesis of phenylhydrazides of N-acylamino acids

1984 ◽  
Vol 49 (11) ◽  
pp. 2557-2561 ◽  
Author(s):  
Václav Čeřovský ◽  
Karel Jošt
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Derivatives Of ◽  
Acyl Derivatives

Phenylhydrazides of Nα-acyl derivatives of all coded amino acids, except proline, were prepared by papain (E.C. 3.4.22.2)-catalyzed synthesis. Comparison of yields affords information about the suitability of the amino acid in position P1 in papain-catalyzed syntheses of peptides.

Synthesis of amino acid derivatives of 5-alkoxy-3,4-dihalo-2(5H)-furanones and their preliminary bioactivity investigation as linkers

2019 ◽  
Vol 17 (20) ◽  
pp. 5138-5147 ◽  
Author(s):  
Shi-He Luo ◽  
Kai Yang ◽  
Jian-Yun Lin ◽  
Juan-Juan Gao ◽  
Xin-Yan Wu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Toxic Effect ◽  
Amino Acid Derivatives ◽  
Metal Free ◽  
Mtt Tests ◽  
Derivatives Of

MTT tests of 2(5H)-furanone derivatives obtained via metal-free C–N coupling show that amino acids as linkers have no toxic effect.

scholarly journals Amino acid derivatives of natural chlorins as a platform for the creation of targeted photosensitizers in oncology

2021 ◽  
Vol 15 (6) ◽  
pp. 16-33
Author(s):  
A. F. Mironov ◽  
P. V. Ostroverkhov ◽  
S. I. Tikhonov ◽  
V. A. Pogorilyy ◽  
N. S. Kirin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Tumor Cells ◽  
Targeted Delivery ◽  
Methionine Sulfoximine ◽  
Amino Acid Derivatives ◽  
Resonance Spectroscopy ◽  
Biochemical Processes ◽  
Derivatives Of

Objectives. This study aims to obtain the amino acid derivatives of chlorophyll a and bacteriochlorophyll a for the targeted delivery of pigments to tumor foci. This will increase biocompatibility and, as a result, reduce toxic side effects. In addition to photodynamic efficiency, an additional cytotoxic effect is expected for the obtained conjugates of photosensitizers (PSs) with amino acids. This is owing to the participation of the latter in intracellular biochemical processes, including interaction with the components of the glutathione antioxidant system, leading to the vulnerability of tumor cells to oxidative stress.Methods. In this work, we have implemented the optimization of the structure of a highly efficient infrared PS based on O-propyloxim-N-propoxybacteriopurpurinimide (DPBP), absorbing at 800 nm and showing photodynamic efficacy for the treatment of deep-seated and pigmented tumors, by introducing L-lysine, L-arginine, methionine sulfoximine (MSO), and buthionine sulfoximine (BSO) methyl esters. The structure of the obtained compounds was proved by mass spectrometry and nuclear magnetic resonance spectroscopy, and the photoinduced cytotoxicity was studied in vitro on the HeLa cell line.Results. Conjugates of DPBP with amino acids and their derivatives, such as lysine, arginine, MSO, and BSO have been prepared. The chelating ability of DPBP conjugate with lysine was shown, and its Sn(IV) complex was obtained.Conclusions. Biological testing of DPBP with MSO and BSO showed a 5–6-fold increase in photoinduced cytotoxicity compared to the parent DPBP PS. Additionally, a high internalization of pigments by tumor cells was found, and the dark cytotoxicity (in the absence of irradiation) of DPBP-MSO and DPBP-BSO increased fourfold compared to the initial DPBP compound. This can be explained by the participation of methionine derivatives in the biochemical processes of the tumor cell.

Synthesis and Fungicidal Activity of Lipophylic N- and O-Acyl Derivatives of β-Hydroxy ᴅʟ-α-Amino Acids

2003 ◽  
Vol 58 (5-6) ◽  
pp. 366-370 ◽  
Author(s):  
Nijole Dirvianskytė ◽  
Juozapas Straukas ◽  
Valdemaras Razumas ◽  
Eugenius Butkus
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Verticillium Dahliae ◽  
Fungicidal Activity ◽  
Growth Of Fungi ◽  
Derivatives Of ◽  
Acyl Derivatives ◽  
Acid Structure ◽  
Long Chain ◽  
Amino Acid Structure

Abstract Synthesis of N- and O-acyl derivatives of ᴅʟ-serine and threo-ᴅʟ-phenylserine was accomplished by a regioselective acylation of the corresponding amino acid. The residues introduced into amino acid structure contain hydrophobic long chain or aromatic, namely lauroyl, myristoyl and phenylacetyl moieties. The fungicidal activity against six strains of fungi was studied. Several compounds were found to be effective against growth of fungi, and Omyristoyl- ᴅʟ-serine 2 and N-phenylacetyl-threo-ᴅʟ-phenylserine 8 completely inhibited the growth of the mycelium of the fungus Verticillium dahliae.

A new double-labelling procedure for determination of amino acid composition: Application to bacteriorhodopsin

1978 ◽  
Vol 56 (6) ◽  
pp. 517-520 ◽  
Author(s):  
H. Kaplan ◽  
D. C. H. Cheng ◽  
G. Oda ◽  
M. Kates
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Amino Acid Mixture ◽  
Acid Mixture ◽  
Amino Acid Derivatives ◽  
Double Labelling ◽  
Tryptophan Residues ◽  
Labelling Procedure ◽  
Derivatives Of

A new double-labelling procedure for amino acid analysis which requires only routine chromatographic equipment is described. When 1-fluoro-2,4-dinitro[3H]benzene is reacted with a mixture of 14C-labelled amino acids followed by reaction with the same 14C-labelled amino acid mixture diluted with an unlabelled sample of amino acids, the 3H: 14C ratio in the resulting 2,4-dinitrophenyl (DNP) amino acid derivatives of the diluted sample will be increased in proportion to the quantity of unlabelled amino acid in the diluted sample. This procedure gave reliable results when applied to the known proteins insulin and lysozyme. The procedure is most advantageous when applied to amino acids which are unstable during acid hydrolysis or present in low molar fractions.When applied to the analysis of the bacteriorhodopsin in Halobacterium cutirubrum, this procedure showed the presence of one histidine residue and four tryptophan residues per mole protein but no cystine or cysteine; in general, the analyses obtained were consistent with those originally reported by Oesterhelt, D. and Stoeckenius, W. (1971) (Nature (London) New Biol. 233, 149–152) for bacteriorhodopsin of H. halobium.

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