A mechanism for bitter taste sensibility in peptides.

Ishibashi, Norio; Kouge, Katsushige; Shinoda, Ichizo; Kanehisa, Hidenori; Okai, Hideo

doi:10.1271/bbb1961.52.819

Cited by 58 publications

(58 citation statements)

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“…The dipeptide 8-amino- [1,4] 2) coupled with two carbonyl carbons at δ 169.9 (C-3) and 164.4 (C-9). We first considered that the structure of this compound corresponded to the diketopiperazine cyclo[Gly-Orn] (2).…”

Section: Resultsmentioning

confidence: 99%

“…We first considered that the structure of this compound corresponded to the diketopiperazine cyclo[Gly-Orn] (2). 4 However, analysis of the NMR data in DMSO-d 6 disfavoured this hypothesis, since a 1 H coupling in the 1 H-1 H COSY spectrum between CH 2 -5 at δ 3.53 with the NH-4 amide exchangeable proton at δ 8.10 was observed. Additionally, both CH 2 -5 at δ 3.53 and NH-4 proton at δ 8.10 showed long-range couplings to the carbonyl group at δ 169.9.…”

Section: Resultsmentioning

confidence: 99%

“…NMR spectra were run either on a 6-amino- [1,4] 1 H and 13 C NMR data: see Table 1. N-acetyltyramine (4). Glassy solid.…”

Section: Methodsmentioning

confidence: 99%

“…Based on 1 H NMR analysis, the crude extract of the actinomycete Streptomyces acrimycini was selected for a chemical investigation. We report here the isolation and structure determination of two new dipeptide metabolites isolated from S. acrimycini: 8-amino- [1,4]diazonane-2,5-dione (1) and leucyl-4-hydroxyproline (3).…”

Section: Introductionmentioning

confidence: 99%

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Dipeptide metabolites from the marine derived bacterium Streptomyces acrymicini

Hernandez¹,

Macedo²,

Berlinck³

et al. 2004

J. Braz. Chem. Soc.

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A investigação química do extrato bruto obtido a partir do meio de crescimento do actinomiceto Streptomyces acrimycini isolado de sedimentos marinhos levou ao isolamento de dois dipeptídeos: a 8-amino-[1,4]diazonano-2,5-diona (1) e leucil-4-hidroxiprolina (3). Os compostos foram isolados a partir do seu meio de crescimento por uma série de etapas cromatográficas e identificados pela análise de seus dados espectroscópicos. O esqueleto macrocíclico da 8-amino-[1,4]diazonano-2,5-diona foi descrito apenas uma vez nas marinobactinas, sideróforos isolados a partir de uma bactéria marinha do gênero Marinobacter.The chemical investigation of the crude extract obtained from the growth media of the marinederived actinomycete Streptomyces acrimycini isolated from marine sediments led to the isolation of two new dipeptide derivatives: 8-amino-[1,4]diazonane-2,5-dione (1) and leucyl-4-hydroxyproline (3). The dipeptides were isolated from the growth media by a series of chromatographic steps, and identified by analysis of spectroscopic data. The macrocyclic carbon backbone of 8-amino-[1,4]diazonane-2,5-dione has been previously reported only once in marinobactins, siderophores isolated from the marine bacterium Marinobacter sp.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…NMR spectra were run either on a 6-amino- [1,4] 1 H and 13 C NMR data: see Table 1. N-acetyltyramine (4). Glassy solid.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Dipeptide metabolites from the marine derived bacterium Streptomyces acrymicini

Hernandez¹,

Macedo²,

Berlinck³

et al. 2004

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…The product was obtained as a hygroscopic powder; 9.62 g yield (95%); Rrl 0.65; Rr2 0.75. (8). Compound 25 (3.49 g, 2 mmol) was dissolved in MeOH (6ml), before the mixture was hydrogenated in the presence of 10% palladium on carbon (2.5 g) at room temperature for 72 h. The filtrate from the catalyst was evaporated, and the resulting oily residue was solidified with the help of acetone-ether to yield 1.22g ofa hygroscopic powder (72%); Rrl 0.02.…”

Section: H-4's(z)-gly-asp(obzl)-glu(obzl)-glu(obzl)-obzl' Hci (24)mentioning

confidence: 99%