On the Absolute Configuration of <i>l</i>-Carnitine (Vitamin B<i>T</i>)

Kaneko, Takeo; Yoshida, Ryonosuke

doi:10.1246/bcsj.35.1153

Cited by 47 publications

(10 citation statements)

References 7 publications

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“…To more conclusively determine the source of the glycine (23), aqueous solutions of the hydrochlorides of analytically pure 4-amino-4-deoxy-D-erythronic acid (3) and 4-amino-4-deoxy-D-threonic acid (5) were treated with excess silver(I) oxide on the steam bath for periods of 15 min to 1.5 h. In each case, glycine (23) was formed in amounts of 8 to 11%. No attempt was made to increase the conversion to glycine by employing vigorous stirring or by using a greater excess of silver(I) oxide.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Musich¹,

Rapoport²

1978

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Musich¹,

Rapoport²

1978

J. Am. Chem. Soc.

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“…They were then tested for their ability to recognize specific biological substrates, such as carnitine. While the unnatural antipode, d -carnitine, is devoid of a recognized biological role, the naturally occurring l -carnitine is involved in fatty acid transport through the formation of fatty acid-carnitine esters. − PL -181 was found to bind l -carnitine with an association constant of (4.1 ± 0.3) × 10 3 M –1 and a 1:1 stoichiometry, as inferred from 1 H NMR spectroscopic analyses carried out in CD 3 CN. Molecular modeling studies led to the suggestion that receptor PL -181 binds l -carnitine in a ditopic fashion with the carnitine carboxylate group stabilized by the cyclic peptide moiety via hydrogen-bonding interactions.…”

Section: Recognition With Macrocyclic Ion Pair Receptorsmentioning

confidence: 91%

Macrocycles as Ion Pair Receptors

et al. 2019

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Cation and anion recognition have both played central roles in the development of supramolecular chemistry. Much of the associated research has focused on the development of receptors for individual cations or anions, as well as their applications in different areas. Rarely is complexation of the counterions considered. In contrast, ion pair recognition chemistry, emerging from cation and anion coordination chemistry, is a specific research field where co-complexation of both anions and cations, so-called ion pairs, is the center of focus. Systems used for the purpose, known as ion pair receptors, are typically di-or polytopic hosts that contain recognition sites for both cations and anions and which permit the concurrent binding of multiple ions. The field of ion pair recognition has blossomed during the past decades. Several smaller reviews on the topic were published roughly 5 years ago. They provided a summary of synthetic progress and detailed the various limiting ion recognition modes displayed by both acyclic and macrocyclic ion pair receptors known at the time. The present review is designed to provide a comprehensive and up-to-date overview of the chemistry of macrocycle-based ion pair receptors. We specifically focus on the relationship between structure and ion pair recognition, as well as applications of ion pair receptors in sensor development, cation and anion extraction, ion transport, and logic gate construction. CONTENTS 3.4.

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“…Later this year, Bremer (1962b) was the first researcher who described the main physiological function of carnitine as carrier for the translocation of long-chain fatty acid from cytoplasmic compartment into mitochondria, where beta-oxidation enzymes are located for energy production. The physiological form of carnitine was identified in 1962 as the L (À) isomer, or levocarnitine (Kaneko and Yoshida, 1962). Since then, the term carnitine has always been referred to as L-carnitine.…”

Section: Historical Backgroundmentioning

confidence: 99%

Role of carnitine in cancer chemotherapy-induced multiple organ toxicity

Sayed‐Ahmed

2010

Saudi Pharmaceutical Journal

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In the last few years, cancer chemotherapy has been successfully employed in the treatment of different types of human tumours. Unfortunately, the optimal clinical usefulness of this important treatment modality is usually limited secondary to the development of life-threatening multiple organ toxicity. Cancer chemotherapy may cause these toxic effects by mechanisms not involved in their anticancer activity that can severely affect the life of patients and represent a direct cause of death. Several experimental and clinical studies have demonstrated that some important anticancer drugs interfere with the absorption, synthesis, and excretion of carnitine in non-tumour tissues, resulting in a secondary carnitine deficiency which is reversed by carnitine treatment without affecting anticancer therapeutic efficacy. Prototypes of anticancer drugs that alter carnitine system are doxorubicin, cisplatin, carboplatin, oxaliplatin, cyclophosphamide and ifosfamide. Furthermore, cachectic cancer patients are especially at risk for carnitine deficiency due to decreased oral intake and/or increased renal losses. Altered serum and urine carnitine levels have been reported in cancer patients with various forms of malignant diseases. Recent studies in our laboratory have demonstrated that carnitine deficiency constitute a risk factor and should be viewed as a mechanism during development of oxazaphosphorines-induced cardiotoxicity in rats. Similarly, inhibition of gene expression of heart fatty acid-binding protein and organic cation/carnitine transporter in doxorubicin cardiomyopathic rat model has been reported. In view of these facts and in view of irreplaceability of these important anticancer drugs, this review aimed to highlight the role of carnitine depletion and supplementation during development of chemotherapy-induced multiple organ toxicity.

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On the Absolute Configuration of l-Carnitine (Vitamin BT)

Cited by 47 publications

References 7 publications

Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima

Macrocycles as Ion Pair Receptors

Role of carnitine in cancer chemotherapy-induced multiple organ toxicity

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