The preparation of dimedone derivatives of amino acids and their use in peptide synthesis

1965 ◽  
Vol 18 (3) ◽  
pp. 417 ◽  
Author(s):  
B Halpern
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Peptide Synthesis ◽  
Catalytic Hydrogenation ◽  
Amino Acid Derivatives ◽  
Alkyl Esters ◽  
Benzyl Esters ◽  
Derivatives Of

The preparation of dimedone derivatives of amino acids has been effected by saponification of the corresponding alkyl esters, and also by catalytic hydrogenation of the respective benzyl esters. The amino acid derivatives have been used to synthesize peptides in excellent yields, employing dicyclohexyl carbodiimide as the condensing agent.

N-Methylamino acids in peptide synthesis. V. The synthesis of N-tert-butyloxycarbonyl, N-methylamino acids by N-methylation

1977 ◽  
Vol 55 (5) ◽  
pp. 906-910 ◽  
Author(s):  
S. T. Cheung ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Room Temperature ◽  
Sodium Hydride ◽  
Amino Acid Derivatives ◽  
Enantiomerically Pure ◽  
Neutral Amino Acids ◽  
Related Data

The preparation of enantiomerically pure N-tert-butyloxycarbonyl,N-methylamino acids by N-methylation of the parent amino acid derivatives using sodium hydride and methyl iodide in tetrahydrofuran at room temperature is described for neutral amino acids including O-benzyl-protected threonine and tyrosine. Methylation of the O-benzylserine derivative under these conditions gives the N-methyldehydroalanine derivative. The β-elimination is completely suppressed, giving the corresponding N-methylserine derivative when the reaction is carried out at 5 °C. Other related data on N-methylation and N-methylamino acid derivatives are presented.

Comparative acidic cleavage experiments with methyl-substituted benzyl esters of amino acids

1967 ◽  
Vol 20 (10) ◽  
pp. 2243 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Amino Acid ◽  
Solid Phase ◽  
Hydrogen Bromide ◽  
Solid Phase Peptide Synthesis ◽  
Amino Acid Derivatives ◽  
Methyl Substitution ◽  
Benzyl Esters ◽  
Layer Chromatography

The action of trifluoroacetic acid and hydrogen bromide in acetic acid, respectively, on the benzyl, p-methylbenzyl, 2,4,6-trimethylbenzyl, and penta-methylbenzyl esters of some amino acid derivatives has been investigated by thin-layer chromatography. Methyl substitution greatly enhances the lability of the ester groups. The possible bearing of the results on solid-phase peptide synthesis is discussed.

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.

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.

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.

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.

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