A new amino acid, nicotianamine, from tobacco leaves

Noma, Masana; Noguchi, Masao; Tamaki, Einosuke

doi:10.1016/s0040-4039(01)96769-3

Cited by 87 publications

(43 citation statements)

References 2 publications

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“…[7] Aze occurs in many other plants, including sugar beet, [8] and in rhizomes of Polygonatum sibiricum and Polygonatum odoratum used as supplements in many foods, including tea. [9] Aze is readily misincorporated into proteins as a substitute for proline 1 in many species, including humans, [10] and causes numerous toxic effects as well as congenital malformations.…”

Section: Introductionmentioning

confidence: 99%

3‐Hydroxyazetidine Carboxylic Acids: Non‐Proteinogenic Amino Acids for Medicinal Chemists

et al. 2013

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The formation from D-glucose of both enantiomers of 2,4-dideoxy-2,4-iminoribonic acid is the first chemical synthesis of unprotected 3-hydroxyazetidine carboxylic acids. The long-term stability of 3-hydroxyazetidine amides is established at acidic and neutral pH and implies their value as non-proteinogenic amino acid components of peptides, providing medicinal chemists with a new class of peptide isosteres. The structure of N,3-O-dibenzyl-2,4-dideoxy-2,4-imino-D-ribonic acid was established by X-ray crystallographic analysis. An N-methylazetidine amide derivative is a specific inhibitor of β-hexosaminidases at the micromolar level, and is only the second example of potent inhibition of any glycosidase by an amide of a sugar amino acid related to an iminosugar.

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Section: Introductionmentioning

confidence: 99%

3‐Hydroxyazetidine Carboxylic Acids: Non‐Proteinogenic Amino Acids for Medicinal Chemists

et al. 2013

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“…6) The non-proteinogenic amino acid nicotianamine (NA) was first found in tobacco 7) and has been found in all plants examined so far, including Strategy I and Strategy II plants. [8][9][10] NA chelate many metal cations such as Fe, zinc (Zn), copper (Cu), and manganese (Mn) [11][12][13] and play important roles in the internal transport of metal nutrients.…”

mentioning

confidence: 99%

Enhanced levels of nicotianamine promote iron accumulation and tolerance to calcareous soil in soybean

Nozoye

Kim

Kakei

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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Iron (Fe) is an essential nutrient in both plants and humans. Fe deficiency on calcareous soil with low Fe availability is a major agricultural problem. Nicotianamine (NA) is one of the Fe chelator in plants, which is involved in metal translocation into seeds, and serves as an antihypertensive substance in humans. In this study, soybean plants overexpressing the barley NA synthase 1 (HvNAS1) gene driven by the constitutive CaMV 35S promoter were produced using Agrobacterium-mediated transformation. The transgenic soybean showed no growth defect and grew normally. The NA content of transgenic soybean seeds was up to four-fold greater than that of non-transgenic (NT) soybean seeds. The level of HvNAS1 expression was positively correlated with the amount of NA, and a high concentration of NA was maintained in the seeds in succeeding generations. The Fe concentration was approximately two-fold greater in transgenic soybean seeds than in NT soybean seeds. Furthermore, the transgenic soybeans showed tolerance to low Fe availability in calcareous soil. Our results suggested that increasing the NA content in soybean seeds by the overexpression of HvNAS1 offers potential benefits for both human health and agricultural productivity.

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“…The reaction mixture was poured into water (10 mL) and extracted with ethyl acetate (3 ϫ 10 mL). The combined organic layer was washed with brine (15 mL), dried with Na 2 SO 4 , and concentrated in vacuo to give 7, which was purified by column chromatography (silica gel; petroleum ether/Et 2 …”

Section: Ses-hse(oses)-otbu (7)mentioning

confidence: 99%

“…[1] This cyclic amino acid is the key component of nicotianamine and mugineic acid derivatives, which are natural potent iron transporters in plants [2] ( Figure 1). Several syntheses of racemic 1 have been reported and reviewed [3] since its first preparation in 1969.…”

Section: Introductionmentioning

confidence: 99%

Direct Access to L‐Azetidine‐2‐carboxylic Acid

2009

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A straightforward synthesis of L‐azetidine‐2‐carboxylic acid is described, leading to both orthogonally protected versions or totally deprotected L‐Aze. The starting material is a commercially available aspartic acid derivative, whose chirality is conserved. The (2‐trimethylsilyl)ethanesulfonyl protecting group (SES) acts as a leaving group on the hydroxy function and serves as an activator for the amine function, which is the key‐step of the reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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A new amino acid, nicotianamine, from tobacco leaves

Cited by 87 publications

References 2 publications

3‐Hydroxyazetidine Carboxylic Acids: Non‐Proteinogenic Amino Acids for Medicinal Chemists

3‐Hydroxyazetidine Carboxylic Acids: Non‐Proteinogenic Amino Acids for Medicinal Chemists

Enhanced levels of nicotianamine promote iron accumulation and tolerance to calcareous soil in soybean

Direct Access to L‐Azetidine‐2‐carboxylic Acid

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