Enantiopure beta3-amino acids-2,2-d2 via homologation of proteinogenic alpha-amino acids.

Abstract:

:A procedure for the synthesis of enantiopure beta3-amino acids from proteinogenic alpha-amino acids, developed by our group a few years ago, has been modified to enable the production of C-2 fully deuterated, C-protected beta3-amino acids and, even more important, the synthesis of valuable deuterium labelled N(Boc)-protected chiral synthons, such as 2-aminoalcohols, 2-aminoiodides, and beta3-amino nitriles.

journal_name

Amino Acids

journal_title

Amino acids

authors

Caputo R,Longobardo L

doi

10.1007/s00726-006-0384-0

subject

Has Abstract

pub_date

2007-01-01 00:00:00

pages

401-4

issue

3

eissn

0939-4451

issn

1438-2199

journal_volume

32

pub_type

杂志文章
  • Quantitative metabolic profiling of NMR spectral signatures of branched chain amino acids in blood serum.

    abstract::Branched Chain Amino Acids (BCAAs) are related to different aspects of diseases like pathogenesis, diagnosis and even prognosis. While in some diseases, levels of all the BCAAs are perturbed; in some cases, perturbation occurs in one or two while the rest remain unaltered. In case of ischemic heart disease, there is a...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1994-1

    authors: Ghosh S,Sengupta A,Chandra K

    更新日期:2015-10-01 00:00:00

  • Prediction and analysis of cell-penetrating peptides using pseudo-amino acid composition and random forest models.

    abstract::Cell-penetrating peptides, a group of short peptides, can traverse cell membranes to enter cells and thus facilitate the uptake of various molecular cargoes. Thus, they have the potential to become powerful drug delivery systems. The correct identification of peptides as cell-penetrating or non-cell-penetrating would ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-1974-5

    authors: Chen L,Chu C,Huang T,Kong X,Cai YD

    更新日期:2015-07-01 00:00:00

  • Antimicrobial activity and membrane-active mechanism of tryptophan zipper-like β-hairpin antimicrobial peptides.

    abstract::Antimicrobial peptides (AMPs) with amphipathic β-hairpin structures have been demonstrated to possess potent antimicrobial activities and great cell selectivities. However, our understanding of β-hairpin antimicrobial peptides lags behind that of α-helices, mainly because it is difficult for short peptides to form rob...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-2029-7

    authors: Xu L,Chou S,Wang J,Shao C,Li W,Zhu X,Shan A

    更新日期:2015-11-01 00:00:00

  • Abomasal infusion of arginine stimulates SCD and C/EBPß gene expression, and decreases CPT1ß gene expression in bovine adipose tissue independent of conjugated linoleic acid.

    abstract::Based on previous research with bovine peadipocytes, we hypothesized that infusion of arginine into the abomasum of Angus steers stimulates stearoyl-CoA desaturase (SCD) gene expression in bovine subcutaneous (s.c.) adipose tissue, and that this would be attenuated by conjugated linoleic acid (CLA). Growing Angus stee...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1622-x

    authors: Choi SH,Wickersham TA,Wu G,Gilmore LA,Edwards HD,Park SK,Kim KH,Smith SB

    更新日期:2014-02-01 00:00:00

  • How are signals transduced across the cytoplasmic membrane? Transport proteins as transmitter of information.

    abstract::In order to adapt to ever changing environmental conditions, bacteria sense environmental stimuli, and convert them into signals that are transduced intracellularly. Several mechanisms have evolved by which receptors transmit signals across the cytoplasmic membrane. Stimulus perception may trigger receptor dimerizatio...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0235-x

    authors: Tetsch L,Jung K

    更新日期:2009-09-01 00:00:00

  • Taurine prevents ethanol-induced apoptosis mediated by mitochondrial or death receptor pathways in liver cells.

    abstract::One pathogenic mechanism of ethanol-induced liver injury is the excessive production of reactive oxygen species (ROS), which may result in alcoholic liver disease (ALD) characterized by cell death due to necrosis and apoptosis. Taurine was proved to protect against liver damage. However, whether taurine attenuates eth...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2561-3

    authors: Wu G,Yang J,Lv H,Jing W,Zhou J,Feng Y,Lin S,Yang Q,Hu J

    更新日期:2018-07-01 00:00:00

  • Regulation of xCT expression and system x (c) (-) function in neuronal cells.

    abstract::The glutamate/cystine antiporter system x(c)(-) transports cystine into cells in exchange for glutamate at a ratio of 1:1. It is composed of a specific light chain, xCT, and a heavy chain, 4F2, linked by a disulfide bridge. Intracellularly, cystine is reduced into cysteine, the rate-limiting precursor of glutathione (...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-011-0862-x

    authors: Lewerenz J,Maher P,Methner A

    更新日期:2012-01-01 00:00:00

  • The effect of taurine and β-alanine supplementation on taurine transporter protein and fatigue resistance in skeletal muscle from mdx mice.

    abstract::This study investigated the effect of taurine and β-alanine supplementation on muscle function and muscle taurine transporter (TauT) protein expression in mdx mice. Wild-type (WT) and mdx mice (5 months) were supplemented with taurine or β-alanine for 4 weeks, after which in vitro contractile properties, fatigue resis...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-016-2292-2

    authors: Horvath DM,Murphy RM,Mollica JP,Hayes A,Goodman CA

    更新日期:2016-11-01 00:00:00

  • The designer leptin antagonist peptide Allo-aca compensates for short serum half-life with very tight binding to the receptor.

    abstract::The leptin receptor antagonist peptide Allo-aca exhibits picomolar activities in various cellular systems and sub-mg/kg subcutaneous efficacies in animal models making it a prime drug candidate and target validation tool. Here we identified the biochemical basis for its remarkable in vivo activity. Allo-aca decomposed...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1650-6

    authors: Otvos L Jr,Vetter SW,Koladia M,Knappe D,Schmidt R,Ostorhazi E,Kovalszky I,Bionda N,Cudic P,Surmacz E,Wade JD,Hoffmann R

    更新日期:2014-04-01 00:00:00

  • A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid.

    abstract::3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymme...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-007-0595-z

    authors: Khalaf JK,Datta A

    更新日期:2008-08-01 00:00:00

  • A comparative study of the chemical reactivity of pyridoxamine, Ac-Phe-Lys and Ac-Cys with various glycating carbonyl compounds.

    abstract::Pyridoxamine (PM) has long been known to inhibit protein glycation via various mechanisms of action. One such mechanism involves the scavenging of carbonyl compounds with glycating ability. Despite the abundant literature on this topic, few quantitative kinetic studies on the processes involved have been reported. In ...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-008-0098-6

    authors: Adrover M,Vilanova B,Frau J,Muñoz F,Donoso J

    更新日期:2009-03-01 00:00:00

  • A potential estrogen mimetic effect of a bis(ethyl)polyamine analogue on estrogen receptor positive MCF-7 breast cancer cells.

    abstract::BE-3-3-3-3 (1,15-(ethylamino)4,8,12-triazapentadecane) is a bis(ethyl)polyamine analogue under investigation as a therapeutic agent for breast cancer. Since estradiol (E(2)) is a critical regulatory molecule in the growth of breast cancer, we examined the effect of BE-3-3-3-3 on estrogen receptor α (ERα) positive MCF-...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1005-0

    authors: Nayvelt I,John S,Hsu HC,Yang P,Liu W,Das G,Hyvönen MT,Alhonen L,Keinänen TA,Shirahata A,Patel R,Thomas T,Thomas TJ

    更新日期:2012-02-01 00:00:00

  • Isozymic nature of spore coat-associated alanine racemase of Bacillus subtilis.

    abstract::Spore coat-associated alanine racemase of Bacillus subtilis, which converts L-alanine to D-alanine, that is, the germinant to the competitive inhibitor, to regulate spore germination for survival of the organism under unfavorable growth conditions, was examined. The dormant spores, L-alanine-initiated germination of w...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s007260070076

    authors: Kanda-Nambu K,Yasuda Y,Tochikubo K

    更新日期:2000-01-01 00:00:00

  • Putrescine overproduction does not affect the catabolism of spermidine and spermine in poplar and Arabidopsis.

    abstract::The effect of up-regulation of putrescine (Put) production by genetic manipulation on the turnover of spermidine (Spd) and spermine (Spm) was investigated in transgenic cells of poplar (Populus nigra × maximowiczii) and seedlings of Arabidopsis thaliana. Several-fold increase in Put production was achieved by expressi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-013-1581-2

    authors: Shao L,Bhatnagar P,Majumdar R,Minocha R,Minocha SC

    更新日期:2014-03-01 00:00:00

  • Ketimine reductase/CRYM catalyzes reductive alkylamination of α-keto acids, confirming its function as an imine reductase.

    abstract::Recently, crystalized mouse ketimine reductase/CRYM complexed with NADPH was found to have pyruvate bound in its active site. We demonstrate that the enzyme binds α-keto acids, such as pyruvate, in solution, and catalyzes the formation of N-alkyl-amino acids from alkylamines and α-keto acids (via reduction of imine in...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-015-2044-8

    authors: Hallen A,Cooper AJ,Smith JR,Jamie JF,Karuso P

    更新日期:2015-11-01 00:00:00

  • Glycine metabolism in animals and humans: implications for nutrition and health.

    abstract::Glycine is a major amino acid in mammals and other animals. It is synthesized from serine, threonine, choline, and hydroxyproline via inter-organ metabolism involving primarily the liver and kidneys. Under normal feeding conditions, glycine is not adequately synthesized in birds or in other animals, particularly in a ...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1493-1

    authors: Wang W,Wu Z,Dai Z,Yang Y,Wang J,Wu G

    更新日期:2013-09-01 00:00:00

  • Synthesis of soluble poly(amide-ether-imide-urea)s bearing amino acid moieties in the main chain under green media (ionic liquid).

    abstract::In this study, an optically active diamine, N,N'-(pyromellitoyl)-bis{N-[4(4-aminophenoxy)phenyl]-2-(4-methyl)pentanamide} (1) containing amino acid L-leucine was prepared in three steps. The step-growth polymerization of this chiral diamine with several diisocyanates in room temperature ionic liquid (IL), 1,3-dipropyl...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-010-0660-x

    authors: Mallakpour S

    更新日期:2011-02-01 00:00:00

  • Electrophysiological effects of exogenous and endogenous kynurenic acid in the rat brain: studies in vivo and in vitro.

    abstract::In this review, recent studies on the electrophysiological effects of de novo synthesized ("endogenous") kynurenic acid (KYNA) are discussed. Endogenous KYNA is normally formed as a byproduct of tryptophan metabolism. Evidence for a physiological role in neuronal excitability has not been strong, in part because brain...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s007260070060

    authors: Scharfman HE,Goodman JH,Schwarcz R

    更新日期:2000-01-01 00:00:00

  • An improved protocol for the preparation of (S)-vinylglycine from (S)-methionine.

    abstract::We present an optimized procedure for the synthesis of (S)-vinylglycine from (S)-methionine. The key step is a solvent free pyrolysis of an intermediate sulfoxide at high temperature. Using our optimized reaction conditions, Cbz-protected vinylglycine was obtained in high yield and with almost no side products. The pr...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0460-3

    authors: Küchenthal CH,Migenda J,Polednia M,Maison W

    更新日期:2010-07-01 00:00:00

  • Coenzyme preference of Streptococcus pyogenes δ1-pyrroline-5-carboxylate reductase: evidence supporting NADPH as the physiological electron donor.

    abstract::The streptococcal enzyme that catalyzes the last step in proline biosynthesis was heterologously expressed and the recombinant protein was purified to electrophoretic homogeneity and characterized thoroughly. As for δ1-pyrroline-5-carboxylate reductases from other sources, it was able to use either NADH or NADPH as th...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-1077-x

    authors: Petrollino D,Forlani G

    更新日期:2012-07-01 00:00:00

  • Lysine metabolism in mammalian brain: an update on the importance of recent discoveries.

    abstract::The lysine catabolism pathway differs in adult mammalian brain from that in extracerebral tissues. The saccharopine pathway is the predominant lysine degradative pathway in extracerebral tissues, whereas the pipecolate pathway predominates in adult brain. The two pathways converge at the level of ∆(1)-piperideine-6-ca...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-013-1590-1

    authors: Hallen A,Jamie JF,Cooper AJ

    更新日期:2013-12-01 00:00:00

  • Effect of natural amino alcohols on the yield of essential amino acids and the amino acid pattern in stressed barley.

    abstract::By application with 2-aminoethanol (2-AE) and choline chloride (CC) in pot experiments the effect of drought stress on barley plants was diminished. In treated plants an increase of the grain yield by 14% (2-AE) and 40% (CC) and a decrease of the stress metabolites glycine betaine and trigonelline was observed. Additi...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00807708

    authors: Bergmann H,Machelett B,Leinhos V

    更新日期:1994-10-01 00:00:00

  • Peptide analogues of 1811-1818 loop of the A3 subunit of the light chain A3-C1-C2 of FVIII of blood coagulation: biological evaluation.

    abstract::Factor VIII, the plasma protein deficient or defective in individuals with hemophilia A, is a critical member of the blood coagulation cascade. Recent studies have identified the FVIII light chain region Glu1811-Lys1818 as being involved in FIXa binding and in the assembly of the FX-activating FIXaz-FVIIIa complex. Ba...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0464-z

    authors: Patsialas K,Koutsas C,Makris P,Liakopoulou-Kyriakides M

    更新日期:2010-07-01 00:00:00

  • Cell growth in arginine- and ornithine-deprived medium and conversion of glutamate to ornithine and arginine in rat hepatoma cells.

    abstract::A subline growing in medium without arginine and ornithine was established from a rat Reuber hepatoma cell line (R-Y121B·cho). The subline designated R-Y117B·cho was able to grow in glutamine, arginine and ornithine-free, glutamate-supplemented medium. Arginine synthesis from glutamate requires four urea cycle enzymes...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/BF00807328

    authors: Yamamoto K,Niwa A

    更新日期:1996-09-01 00:00:00

  • Complete sequencing of the recombinant granulocyte-colony stimulating factor (filgrastim) and detection of biotinylation by mass spectrometry.

    abstract::Granulocyte-colony stimulating factor stimulates production and antibacterial function of neutrophiles. Therapy using the recombinant protein drug represents a major step forward in oncology. The protein has not been, however, completely sequenced at the protein level and this formed the rationale of the current study...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-009-0312-1

    authors: Ahmed KE,Chen WQ,John JP,Kang SU,Lubec G

    更新日期:2010-04-01 00:00:00

  • Acute regulation of IGF-I by alterations in post-exercise macronutrients.

    abstract::This investigation sought to examine the contributions of exercise and nutrient replenishment on in vivo regulation of the insulin-like growth factor-I (IGF-I) axis components. Eight college-aged males completed three high-intensity interval training (HIIT) protocols followed by three post-exercise nutritional protoco...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-011-0837-y

    authors: Foster EB,Fisher G,Sartin JL,Elsasser TH,Wu G,Cowan W,Pascoe DD

    更新日期:2012-04-01 00:00:00

  • Acetaminophen reduces the protein levels of high affinity amino acid permeases and causes tryptophan depletion.

    abstract::In yeast, toxicity of acetaminophen (APAP), a frequently used analgesic and antipyretic drug, depends on ubiquitin-controlled processes. Previously, we showed a remarkable overlap in toxicity profiles between APAP and tyrosine, and a similarity with drugs like rapamycin and quinine, which induce degradation of the ami...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-018-2613-8

    authors: Huseinovic A,Dekker SJ,Boogaard B,Vermeulen NPE,Kooter JM,Vos JC

    更新日期:2018-10-01 00:00:00

  • Tyrosine-kinases in bacteria: from a matter of controversy to the status of key regulatory enzymes.

    abstract::When considering protein phosphorylation in bacteria, phosphorylation of aspartic acid and histidine residues mediated by the two-component systems is the first to spring to mind. And yet other phosphorylation systems have been described in bacteria in the past 20 years including eukaryotic-like serine/threonine kinas...

    journal_title:Amino acids

    pub_type: 杂志文章,评审

    doi:10.1007/s00726-009-0237-8

    authors: Bechet E,Guiral S,Torres S,Mijakovic I,Cozzone AJ,Grangeasse C

    更新日期:2009-09-01 00:00:00

  • Disturbance of erythrocyte lipid bilayer by amino acid-based surfactants.

    abstract::In an attempt to increase our knowledge regarding the mechanisms of surfactant membrane interaction, we studied the action of several anionic and cationic amino acid-based surfactants on membrane fluidity using fluorescence anisotropy. Anisotropy measurements demonstrated that almost all of the surfactants studied dis...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-006-0447-2

    authors: Martínez V,Sánchez L,Busquets MA,Infante MR,Pilar Vinardell M,Mitjans M

    更新日期:2007-09-01 00:00:00

  • Lipid metabolism in pigs fed supplemental conjugated linoleic acid and/or dietary arginine.

    abstract::We proposed that the combination of conjugated linoleic acid (CLA) and arginine would decrease adiposity by depressing lipid synthesis in liver and adipose tissues of growing pigs. Pigs were allotted to treatments in a 2 × 2 factorial design with two lipids (CLA or canola oil) and two amino acids [L-arginine or L-alan...

    journal_title:Amino acids

    pub_type: 杂志文章

    doi:10.1007/s00726-012-1255-5

    authors: Go G,Wu G,Silvey DT,Choi S,Li X,Smith SB

    更新日期:2012-10-01 00:00:00