• Title/Summary/Keyword: Amino acid ester

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Synthesis of N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester Derivatives and their Anticancer Activity (N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester류의 合成 및 抗癌 作用 評價)

  • Kim, Jeong-Gyun;Park, Moon-Tae;Shin, Hong-Dae;Koh, Young-Sim;Yoon, Ung-Chan;Ryu, Sung-Ho;Moon, Kyung-Ho;Kim, Min-Sook
    • YAKHAK HOEJI
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    • v.28 no.4
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    • pp.197-206
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    • 1984
  • The derivatives of N-(alkylcarbamoyl) amino acid methyl ester, N-(2-chloroethylcarbamoyl)-glycine methyl ester (7a), -valine methyl ester (8a), -phenylalanine methyl ester (9a), N-(N'-methylcarbamoyl)-glycine methyl ester (7b), -valine methyl ester (8b), and-phenylalanine methyl ester (9b), were prepared by reacting the corresponding free amino acid methyl ester (glycine-, valine-, phenylalanine-methyl ester) with isocyanate (R-N=C=O${\cdot};R=Cl-CH_2-CH_2-or\; CH_3-)$. The prepared N-(alkylcarbamoyl) amino acid methyl esters (7,8,9) were treated with $NaNO_2$/98% HCOOH in order to obtain their nitrosoated products, N-(alkyl-N'-nitrosocarbmoyl)amino acid methyl ester. The compound (7,8,9) gave N-(2-chloroethyl-N'-nitrosocarbamoyl)-valine methyl ester (14a),-phenylalanine methyl ester (15a), N-(N'-alkyl-N'-nitrosocarbamoyl)-glycine methyl ester (13b),-valine methyl ester. (14b), and-phenylalanine methyl ester (15b) respectively under the nitrosoation. On the other hand, N-(2-chloroethylcarbamoyl) glycine methyl ester produced N-(2-chloroethylcarbamoyl)-N-nitrosoglycine methyl ester (13a). The inhibitory activity of the prepared N-(alkylcarbamoyl) amino acid methyl ester (7,8,9) and N-(alkyl-N'-nitrosocarbamoyl) amino acid methyl ester (13,14,15) towards the growth of L1210 murine leukemia cells were examined. Among them the compound (14a) and (15a) exhibit excellent activity having $ED_{50}\; to\;be\;1.5{\mu}g/ml\;and\;3.0{\mu}g/ml respectively.

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Synthesis of Peptides Containing Optically Active 2-Amino-3-Phosphonopropionic Acid (광학 활성 2-Amino-3-Phosphonopropionic Acid의 새로운 합성 방법과 그를 포함하는 펩티드의 합성)

  • Kim Sang Bum;Cho Sung Ki;Han Jeong Sik;Kim Yong Joon;Hong Suk-In
    • Journal of the Korean Chemical Society
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    • v.38 no.7
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    • pp.516-520
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    • 1994
  • New synthetic method of optically active 2-amino-3-phosphonopropionic acid from L-serine was developed and their phosphonotripeptides, phthalylglycylglycyl-2-amino-3-(diethylphosphono)-propionic acid methyl ester and phthalylglycyl-L-phenylalanyl-2-amino-3-(diethylphosphono)propionic acid methyl ester, were synthesized by coupling reaction of amino acids with 2-amino-3-phosphonopropionic acid methyl ester.

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Nalidixic Acid Prodrugs: Amides from amino acid ester and nalidixic acid

  • Taori, Ashish;Nema, Rajesh;Kohli, D.V.;Uppadhyay, R.K.
    • Archives of Pharmacal Research
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    • v.14 no.1
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    • pp.48-51
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    • 1991
  • Amides from amino acid ester and nalidixic acid were synthesized. The solubility characteristics and partition coefficient of the compounds were studied. The hydrolysis of the compounds was studied in the simulated gastric fluid and simulated intestinal fluid. Some compounds showed better antibacterial activity than nalidixic acid.

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Synthesis of N-acyl-α-aminosuccinimides and N-acyl-α-aminoglutarimides (N-아실-α-아미노숙신이미드와 N-아실-α-아미노글루탈이미드의 합성)

  • 정대일;김문주;송현애;김윤영;이용균;박유미;최순규;한정태;박민수
    • Journal of Life Science
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    • v.14 no.1
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    • pp.91-97
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    • 2004
  • As a part of our study on the improvement of anticonvulsant, here we report the synthesis of N-acyl-$\alpha$-aminosuc-cinimides 1 and N-acyl-$\alpha$-aminoglutarimides 2. (R)-Benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylester 6a, (R)-4-nifro-benzoic acid 4-benzyloxycarbonylamino-2- oxo-pyrrolidin-1-yl ester 6b, (R) -4-nitro-benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6c, and (R)-propionic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6d were synthesized from (R)-2-benzyloxy carbonylamino-succinic acid 3 as a starting meterial. (R)-(3- Benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid methyl ester 10a, (R)-(3-benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid ethy1 ester 10b, an d (R)-2-(3-benzyloxycarbonylamino-2,6- diox o-piperidin-1-yl oxy)-propionic acid methyl ester l0c were synthesized from (R)- 3-carbobenzyloxy-amino-glutarmic acid 7 as a starting meterial. The yield, mp, IR, $^1H-NMR,\; and^{13}C$- NMR spectra of the products 6a, 6b, 6c, 6d, 10a, l0b, l0c are summarized in footnote. The biological studies of these compounds are in progress and will be reported in future.

A Charge-Transfer Effect in Solid Phase Peptide Synthesis: Unsusally High Reactivity in Peptide Bond Formation between p-Nitrobenzophenone Oxime Resin Ester and Amino Acid 4-(Methylthio)phenyl Ester

  • Park, Dong-Hyun;Jung, Jae-Kyu;Lee, Yoon-Sik
    • Bulletin of the Korean Chemical Society
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    • v.9 no.6
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    • pp.394-398
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    • 1988
  • Unusually high reactivity was found in peptide bond formation between p-nitrobenzophenone oxime resin (I) ester and amino acid 4-(methylthio)phentyl (MTP) esters. A charge-transfer complex between the two phenyl rings of the oxime resin (I) and the incoming amino acid MTP esters was considered to be responsible to accelerate the aminolysis reaction of the peptide oxime resin ester. Several di-, tri-, and pentapeptide fragments for preparing enkephalin and glutathione oligomers were successfully prepared in short times.

Liquid Chromatographic Resolution of α-Amino Acid Esters as Benzophenone Imine Derivatives (아미노산 에스테르의 벤조피논 이민 유도체의 액체 크로마토그래피의 광학분리)

  • Yun, Won-Nam;Xu, Wen Jun;Huang, Hu;Lee, Won-Jae
    • KSBB Journal
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    • v.27 no.3
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    • pp.167-171
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    • 2012
  • A convenient liquid chromatographic enantiomer separation of several ${\alpha}$-amino acid esters as benzophenone Schiff base derivatives on covalently immobilized chiral stationary phases (CSPs) derived from polysaccharide derivatives was developed. The benzophenone imine derivatives of ${\alpha}$-amino acid esters were readily prepared by stirring benzophenone imine and the ${\alpha}$-amino acid ester hydrochloride salts in 2-propanol. The chromatographic conditions used on all CSPs were 0.5% or 5% 2-propanol/hexane (V/V) as the mobile phases at 1 mL/min of flow rate and UV 254 nm detection. The performance of Chiralpak IC among all CSPs was superior to that of the other CSPs for resolution of benzophenone imine derivatives of ${\alpha}$-amino acid esters. It is expected that the developed analytical method will be useful for enantiomer resolution of other ${\alpha}$-amino acid esters as benzophenone Schiff base derivatives.

Enantiomer Separation of α-Amino Acid Esters as Nitrobenzoxadiazole Derivatives Using Chiral Columns (키랄 컬럼을 사용한 아미노산 에스테르의 니트로벤조옥사디아졸 유도체의 광학분리)

  • Yun, Won Nam;Kim, Ji Yeon;Lee, Wonjae
    • KSBB Journal
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    • v.28 no.6
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    • pp.423-427
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    • 2013
  • A new convenient derivatization method of ${\alpha}$-amino acid esters as nitrobenzoxadiazole (NBD) derivatives for chiral resolution was introduced and the enantiomer separation of ${\alpha}$-amino acid esters as NBD derivatives was performed by normal HPLC using chiral columns based on polysaccharide derivatives. The NBD derivatives were readily prepared by stirring NBD-Cl and ${\alpha}$-amino acid methyl ester HCl with $NaHCO_3$ in ethanol. The performance of Chiralpak IA was superior to the other chiral stationary phases for enantiomer resolution of NBD derivatives of several ${\alpha}$-amino acid methyl esters. Owing to fluorescence detection as well as strong UV absorption, it is expected that the convenient analytical method developed in this study will be very useful for enantiomer separation of ${\alpha}$-amino acid esters as NBD derivatives on polysaccharide-derived chiral columns.

Chromatographic Enantiomer Separation and Determination of Optical Purity for α-Amino Acid Esters as 9-Anthraldimine Derivatives Using Polysaccharide Based Chiral Columns (다당 유도체를 기초로 한 키랄 컬럼에서 아미노산 에스테르의 안트르알디민 유도체의 광학분리 및 광학순도 측정)

  • Huang, Hu;Jin, Jing-Yu;Lee, Won-Jae
    • KSBB Journal
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    • v.26 no.2
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    • pp.139-142
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    • 2011
  • The chromatographic enantiomer separation of 9-anthraldimine derivatives of ${\alpha}$-amino acid methyl and ethyl esters on four polysaccharide based chiral columns was performed. The 9-anthraldehyde Schiff base derivatives of ${\alpha}$- amino acid esters were readily synthesized by stirring the ${\alpha}$- amino acid ester hydrochloride salts with 9-anthraldehyde in the presence of 1,8-diazabicyclo [5.4.0]undec-7-ene as a base and anhydrous $MgSO_4$. Chiralcel OD or Chiralcel OD-H showed the greatest enantiomer resolution of 9-anthraldimine derivatives of ${\alpha}$-amino acid methyl and ethyl esters. The L-enantiomers of all the analytes were preferentially retained on Chiralcel OD or Chiralcel OD-H. This analytical method was applied in the determination of optical purities of several commercially available D- or L-${\alpha}$-amino acid methyl esters.

Dynamic Kinetic Resolution of α-Bromo Carboxylic Acid Derivatives in Asymmetric Nucleophilic Substitution with Chiral α-Amino Esters

  • Chang, Ji-Yeon;Shin, Eun-Kyoung;Kim, Hyun-Jung;Kim, Yong-Tae;Park, Yong-Sun
    • Bulletin of the Korean Chemical Society
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    • v.26 no.6
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    • pp.989-992
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    • 2005
  • Dynamic kinetic resolution of $\alpha$-bromo carboxylic acid derivatives in nucleophilic substitution with chiral $\alpha$-amino ester nucleophiles in the presence of TBAI and DIEA has been investigated for stereoselective syntheses of 1,1'-iminodicarboxylic acid derivatives. Nucleophilic substitutions with various chiral $\alpha$-amino esters gave iminodiacetates 2-8 with stereoselectivities up to 87 : 13 dr. Also, the reactions of N-($\alpha$-bromo-$\alpha$-phenylacetyl)-L-alanine methyl ester with L-alanine, D-alanine and glycine methyl ester nucleophiles afforded N-carboxyalkyl dipeptide analogues 10-12 up to 90 : 10 dr.