Publications by authors named "Ka-Ho Lee"

21 Publications

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Mechanistic study on the reaction of pinB-BMes with alkynes based on experimental investigation and DFT calculations: gradual change of mechanism depending on the substituent.

Chem Sci 2021 Jul 17;12(28):9806-9815. Epub 2021 Jun 17.

Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University Furo-cho, Chikusa-ku Nagoya Aichi 464-8603 Japan

Transition metal-free direct and base-catalyzed 1,2-diborations of arylacetylenes using pinB-BMes provided a /-isomeric mixture of diborylalkenes. The kinetic analysis showed that the reaction rate and isomer ratio were affected by reaction conditions and substituents on the aryl ring. DFT calculations indicated that direct addition proceeded the interaction of acetylene-π with the BMes fragment. In contrast, for the base-catalyzed diboration, the previously isolated sp-sp diborane and borataallene were confirmed as stable intermediates by calculations. The whole reaction pathways can be divided into the Bpin-migration and deprotonation steps, where the borataallene should be considered as a common intermediate. It should be noted that the deprotonation step is reversible and affords the kinetically less favoured isomer under the thermodynamic conditions. As a result, the composition of isomeric products, in the base-catalyzed diboration, is attributed to the small difference of activation barriers between direct and base-catalyzed systems.
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http://dx.doi.org/10.1039/d1sc02863dDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8293998PMC
July 2021

Clinical and pathological characterization of FLNC-related myofibrillar myopathy caused by founder variant c.8129G>A in Hong Kong Chinese.

Clin Genet 2020 05 23;97(5):747-757. Epub 2020 Feb 23.

Department of Pathology, Queen Elizabeth Hospital, Hong Kong.

FLNC-related myofibrillar myopathy could manifest as autosomal dominant late-onset slowly progressive proximal muscle weakness; involvements of cardiac and/or respiratory functions are common. We describe 34 patients in nine families of FLNC-related myofibrillar myopathy in Hong Kong ethnic Chinese diagnosed over the last 12 years, in whom the same pathogenic variant c.8129G>A (p.Trp2710*) was detected. Twenty-six patients were symptomatic when diagnosed; four patients died of pneumonia and/or respiratory failure. Abnormal amorphous material or granulofilamentous masses were detected in half of the cases, with mitochondrial abnormalities noted in two-thirds. We also show by haplotype analysis the founder effect associated with this Hong Kong variant, which might have occurred 42 to 71 generations ago or around Tang and Song dynasties, and underlain a higher incidence of myofibrillar myopathy among Hong Kong Chinese. The late-onset nature and slowly progressive course of the highly penetrant condition could have significant impact on the family members, and an early diagnosis could benefit the whole family. Considering another neighboring founder variant in FLNC in German patients, we advocate development of specific therapies such as chaperone-based or antisense oligonucleotide strategies for this particular type of myopathy.
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http://dx.doi.org/10.1111/cge.13715DOI Listing
May 2020

Synthesis, Characterization and Electronic Structure of Dirhenadehyro[12]annulene Complexes.

Chempluschem 2019 Jan 13;84(1):85-91. Epub 2018 Dec 13.

Department of Chemistry, The Hong Kong University of Science and Technology Clear Water Bay, Kowloon, Hong Kong, P. R. China.

Treatment of the SiMe -protected dichloro-rhenium carbyne complexes Re{≡CCH=C(R)C≡CSiMe }Cl (PMe Ph) (R = CMe , 1-adamantyl) with CsF in methanol directly afforded the 12-membered metallacycles {ReCl(PMe Ph) } {≡CCH=C(R)C≡C-} . The electronic structure of the metallacycle was investigated by density functional calculations. The UV-vis spectrum of the metallacycle shows a red-shifted band compared to that of the starting dichlorocarbyne complex. Treatment of {ReCl(PMe Ph) } {≡CCH=C(CMe )C≡C-} with HCl produced the dichloro-rhenium carbyne complex Re{≡CCH=C(CMe )C≡CH}Cl (PMe Ph) , which is consistent with the electronic structure of the 12-membered metallacycles.
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http://dx.doi.org/10.1002/cplu.201800537DOI Listing
January 2019

Facile synthesis of polycyclic metallaarynes.

Chem Sci 2018 Jul 19;9(27):5994-5998. Epub 2018 Jun 19.

Department of Chemistry , Hong Kong University of Science and Technology , Clear Water Bay , Kowloon , Hong Kong . Email: ; Email: ; Email:

Metalla-analogs of polycyclic arynes represent an interesting class of metallaaromatics with a formal M[triple bond, length as m-dash]C bond within the ring. The first examples of a bicyclic β-metallaaryne and tricyclic metallaarynes, including a metallaanthracyne and a metallaphenanthryne, were obtained in good yields by reactions of OsCl(PPh) with alkyne-functionalized phosphorus ylides.
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http://dx.doi.org/10.1039/c8sc02086hDOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6050526PMC
July 2018

DFT Studies of Dimerization Reactions of Boroles.

Chemistry 2017 Aug 3;23(48):11587-11597. Epub 2017 Aug 3.

Department of Chemistry, The Hong Kong University of Science and Technology, Hong Kong.

Boroles undergo dimerization reactions to give Diels-Alder (DA) dimers, bridged-bicyclic (BB) dimers or spiro dimers (SD) depending on the substituents on the borole. We performed DFT calculations to investigate how different substituents at the carbon atoms of the butadiene backbone as well as at the boron atom influence the dimerization reaction pathways. The DFT results show that, in general, both the DA and BB dimers are easily accessible kinetically, and the DA dimers are thermodynamically more stable than the BB dimers. When the substituent-substituent repulsive steric interactions are alleviated to a certain extent, the BB dimers are more stable than the DA dimer, and become accessible. The SD dimers are generally kinetically difficult to obtain. However, we found that aryl substituents promote the formation of the SD dimers.
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http://dx.doi.org/10.1002/chem.201701737DOI Listing
August 2017

The "flipped classroom" approach: Stimulating positive learning attitudes and improving mastery of histology among medical students.

Anat Sci Educ 2017 Jul 4;10(4):317-327. Epub 2016 Nov 4.

Division of Histology and Embryology, Jinan University School of Medicine, Guangzhou, People's Republic of China.

Traditional medical education methodologies have been dramatically impacted by the introduction of new teaching approaches over the past few decades. In particular, the "flipped classroom" format has drawn a great deal of attention. However, evidence regarding the effectiveness of the flipped model remains limited due to a lack of outcome-based studies. In the present study, a pilot histology curriculum of the organ systems was implemented among 24 Traditional Chinese Medicine (TCM) students in a flipped classroom format at Jinan University. As a control, another 87 TCM students followed a conventional histology curriculum. The academic performance of the two groups was compared. In addition, a questionnaire was administered to the flipped classroom group. The test scores for the flipped classroom participants were found to be significantly higher compared to non-participants in the control group. These results suggest that students may benefit from using the flipped classroom format. Follow-up questionnaires also revealed that most of the flipped classroom participants undertook relatively more earnest preparations before class and were actively involved in classroom learning activities. The teachers were also found to have more class time for leading discussions and delivering quizzes rather than repeating rote didactics. Consequently, the increased teaching and learning activities contributed to a better performance among the flipped classroom group. This pilot study suggests that a flipped classroom approach can be used to improve histology education among medical students. However, future studies employing randomization, larger numbers of students, and more precise tracking methods are needed before definitive conclusions can be drawn. Anat Sci Educ 10: 317-327. © 2016 American Association of Anatomists.
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http://dx.doi.org/10.1002/ase.1664DOI Listing
July 2017

Cleaving Dihydrogen with Tetra(o-tolyl)diborane(4).

J Am Chem Soc 2017 02 10;139(7):2593-2596. Epub 2017 Feb 10.

Department of Applied Chemistry, Graduate School of Engineering, Nagoya University , Furo-cho, Chikusa-ku, Nagoya, 464-8603 Aichi, Japan.

Tetra(o-tolyl)diborane(4), 1, was synthesized and characterized experimentally as well as theoretically by density functional theory (DFT) calculations. Exposure of 1 to H (1 bar) at room temperature afforded the corresponding di(o-tolyl)hydroborane through cleavage of the H-H and B-B bonds. DFT calculations suggested a diarylboryl anion character for the transition state.
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http://dx.doi.org/10.1021/jacs.7b00924DOI Listing
February 2017

A Potassium Diboryllithate: Synthesis, Bonding Properties, and the Deprotonation of Benzene.

Angew Chem Int Ed Engl 2016 09 17;55(38):11426-30. Epub 2016 Aug 17.

Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, 113-8656, Tokyo, Japan.

A potassium diboryllithate (B2 LiK) was synthesized and structurally characterized. DFT calculations, including NPA and AIM analyses of B2 LiK, revealed ionic interactions between the two bridging boryl anions and Li(+) and K(+) . Upon standing in benzene, B2 LiK deprotonated the solvent to form a hydroborane and a phenylborane. On the basis of DFT calculations, a detailed reaction mechanism, involving deprotonation and hydride/phenyl exchange processes, is proposed. An NBO analysis of the transition state for the deprotonation of benzene suggests that the deprotonation should be induced by the coordination of benzene to the K(+) .
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http://dx.doi.org/10.1002/anie.201605005DOI Listing
September 2016

Direct and Base-Catalyzed Diboration of Alkynes Using the Unsymmetrical Diborane(4), pinB-BMes2.

J Am Chem Soc 2016 05 11;138(20):6662-9. Epub 2016 May 11.

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University , 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

In the absence of transition metal catalysts, the unsymmetrical diborane(4), pinB-BMes2, reacted with alkynes to afford diborylalkenes. The isomer ratio of the products could be controlled via temperature, solvent, and additive(s). A reaction mechanism was proposed on the basis of two isolated intermediates, and this reaction could furthermore be applied to synthesize a luminescent molecule.
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http://dx.doi.org/10.1021/jacs.6b03686DOI Listing
May 2016

Synthesis and Characterization of Dirhenadehydro[12]annulenes.

Angew Chem Int Ed Engl 2016 06 29;55(25):7194-8. Epub 2016 Apr 29.

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.

The 12-membered-ring metallacycles [mer-Re{≡CCH=C(R)C≡C-}Cl(PMe2 Ph)3 )]2 (R=CMe3 , 1-adamantyl), which are organometallic analogues of antiaromatic octadehydro[12]annulene, are prepared by heating the methyl carbyne complexes mer-Re{≡CCH=C(R)C≡CH}(CH3 )Cl(PMe2 Ph)3 . An intermolecular σ-bond metathesis between the Re-CH3 bond and the acetylenic C-H bond is proposed for their formation.
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http://dx.doi.org/10.1002/anie.201601562DOI Listing
June 2016

Dexamethasone Exposure Accelerates Endochondral Ossification of Chick Embryos Via Angiogenesis.

Toxicol Sci 2016 Jan 14;149(1):167-77. Epub 2015 Oct 14.

*Department of Histology & Embryology, Joint Lab for Brain Function and Health, School of Medicine, Jinan University, Guangzhou 510632, China; Institute of Fetal-Preterm Labor Medicine, Jinan University, Guangzhou 510632, China

Dexamethasone (Dex) is widely used to treat chronic inflammatory diseases in the clinic. Increasingly, there is more attention being paid to the side effect of Dex. In this study, we investigated the involvement and mechanism of Dex exposure in accelerating mineralization during long bone formation. We first determined that Dex exposure could accelerate long bone mineralization in vivo, but there was no apparent difference between control and Dex-treated in the phalanges model in vitro. Next, we established that Dex exposure promoted angiogenesis in the chick yolk sac membrane model. In addition, it increased human umbilical vein endothelial cell proliferation and migration in culture. We found that Dex could enhance angiogenesis when phalanges were cultured on chick chorioallantoic membrane and correspondingly increased the expression of angiogenesis-related genes in the phalanges. Furthermore, we also revealed that Dex exposure reduced the number of osteoblasts and simultaneously increased the number of osteocytes in ex vivo-cultured phalanges. Runx-2 and Col10α1 expressions were up-regulated by Dex exposure, indicating that Dex exposure accelerated the terminal differentiation of osteoblasts. Lastly, we demonstrated that MC3T3-E1 cells cultured in the presence of Dex accelerated their mineralization. In summary, we have shown that the ability of Dex to initiate angiogenesis is the mechanism that allows it to accelerate mineralization during long bone formation.
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http://dx.doi.org/10.1093/toxsci/kfv227DOI Listing
January 2016

Lowering the reduction potential of a boron compound by means of the substituent effect of the boryl group: one-electron reduction of an unsymmetrical diborane(4).

Chemistry 2015 Mar 29;21(11):4267-71. Epub 2015 Jan 29.

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27, Kasuga, Bunkyo-ku, 112-8551 Tokyo (Japan) http://www.chem.chuo-u.ac.jp/∼element/index-e.html.

We have clarified and observed the high electron affinity of pinB-BMes2 (1; Mes = mesityl, pin = pinacolato). By using electrochemistry, it was shown that 1 has a higher electron affinity than those of B2pin2 and Mes3B. One-electron reduction of 1 gave the corresponding radical anion. The ESR spectroscopy and DFT calculation revealed the unsymmetrical distribution of electron density over the B-B bond. UV/Vis spectroscopy showed that the SOMO-related absorption supports the deep purple color of the radical anion. DFT studies on the torsion angle dependency of the LUMO levels and relative energies revealed the reason why 1 has high electron affinity as a result of the substituent effect of the Bpin group.
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http://dx.doi.org/10.1002/chem.201406609DOI Listing
March 2015

Highly efficient tetradentate ruthenium catalyst for ester reduction: especially for hydrogenation of fatty acid esters.

Org Lett 2015 Feb 12;17(3):454-7. Epub 2015 Jan 12.

College of Chemistry and Molecular Sciences, Wuhan University , Wuhan 430072, People's Republic of China.

A new tetradentate ruthenium complex has been developed for hydrogenation of esters. The catalyst's structure features a pyridinemethanamino group and three tight chelating five-membered rings. The structure character is believed to be responsible for its high stability and high carbonylation-resistant properties. Thus, this catalyst shows outstanding performance in the catalytic hydrogenation of a variety of esters, especially for fatty acid esters, which may be used in practical applications. New insight on designing hydrogenation catalyst for reducing esters to alcohols has been provided through theoretical calculations.
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http://dx.doi.org/10.1021/ol503456jDOI Listing
February 2015

Weil's disease presenting as atypical pneumonia.

Acute Med 2014 ;13(4):178-81

Consultant Acute Medicine and Elderly Care Physician, Chelsea and Westminster Hospital.

Leptospirosis is a disease caused by spp. Leptospira, also known as Weil's disease if it manifests with jaundice. It can be associated with respiratory, renal, hepatic and haematological complications and most importantly carries a high mortality when untreated. We describe a case of a 53 year old man presenting with myalgia and fever in whom the diagnosis of leptospirosis was not initially considered. Following a deterioration in his condition a careful history revealed an apparent brief exposure to animal urine and subsequent grossly positive Leptospira serology. Treatment of his condition led to complete resolution after a brief stay on the intensive care unit. This case highlights the atypical nature of a presentation of Leptospirosis, its respiratory complications, and importance of serological testing in its diagnosis.
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September 2015

Synthesis of rhenabenzenes from the reactions of rhenacyclobutadienes with ethoxyethyne.

Chemistry 2014 Nov 12;20(45):14885-99. Epub 2014 Sep 12.

Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon (Hong Kong), Fax: (+852) 2358-1594.

Treatment of Na[Re(CO)5 ] with RCCCO2 Et (R=phenyl, naphthalen-1-yl, phenanthren-9-yl and pyren-1-yl) followed by reaction with acetyl chloride and ethanol afforded the rhenacyclobutadienes Re{-C(R)C(CO2 Et)C(OEt)}(CO)4 . Reactions of these rhenacyclobutadienes with HCCOEt produced rhenabenzenes Re{-C(R)C(CO2 Et)C(OEt)CHC(OEt)}(CO)4 . Except for R=Ph, new rhenacyclobutadienes with pendant alkenyl substituents Re{-C(R)C(C(OEt)CH(CO2 Et))C(OEt)}(CO)4 were also isolated from these reactions. The NMR spectroscopic and X-ray structural data, as well as the aromatic stabilization energy (ASE) values suggest that the rhenabenzenes are aromatic, with extensive delocalized π character.
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http://dx.doi.org/10.1002/chem.201403186DOI Listing
November 2014

Facile scission of isonitrile carbon-nitrogen triple bond using a diborane(4) reagent.

Nat Commun 2014 Jun 26;5:4245. Epub 2014 Jun 26.

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku 112-8551, Japan.

Transition metal reagents and catalysts are generally effective to cleave all three bonds (one σ and two π) in a triple bond despite its high bonding energy. Recently, chemistry of single-bond cleavage by using main-group element compounds is rapidly being developed in the absence of transition metals. However, the cleavage of a triple bond using non-transition-metal compounds is less explored. Here we report that an unsymmetrical diborane(4) compound could react with carbon monoxide and tert-butyl isonitrile at room temperature. In the latter case, the carbon-nitrogen triple bond was completely cleaved in the absence of transition metal as confirmed by X-ray crystallographic analysis, (13)C NMR spectroscopy with (13)C labelling and DFT calculations. The DFT calculations also revealed the detailed reaction mechanism and indicated that the key for the carbon-nitrogen triple-bond cleavage could be attributed to the presence of nucleophilic nitrogen atom in one of the intermediates.
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http://dx.doi.org/10.1038/ncomms5245DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4083417PMC
June 2014

Structural revision of cephalosporolide J and bassianolone.

J Org Chem 2014 Feb 22;79(3):1493-7. Epub 2014 Jan 22.

Department of Chemistry, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong, China.

The NMR spectra for three "natural" products: cephalosporolide C (Ces-C), cephalosporolide J (Ces-J), and bassianolone were found to be identical, and we proposed that Ces-C was the correct structure for the reported spectra. The first total synthesis of the proposed structure for Ces-J was achieved to support our structural revision for Ces-J. Chemical transformations of bassianolone and computational prediction of (13)C NMR spectra allowed us to conclude that Ces-C was the correct structure for bassianolone. Our synthetic and computational studies suggested that these "different" natural products Ces-C, Ces-J, and bassianolone have the same structure: Ces-C.
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http://dx.doi.org/10.1021/jo402602hDOI Listing
February 2014

Absence of paternal accessory sex glands dysregulates preimplantation embryo cell cycle and causes early oviductal-uterine transit in the golden hamster in vivo.

Fertil Steril 2008 Apr 14;89(4):1021-4. Epub 2007 Nov 14.

Department of Anatomy, Faculty of Medicine, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong.

We hypothesize that deletion of paternal accessory sex glands compromised developmental potential of preimplantation embryos because of dysregulation of blastomeric cell cycle regulators. Quantification by immunocytochemistry showed disrupted cyclicity of proliferating cell nuclear antigen, augmented p53 and p21 expression, and premature transit from oviduct to uterus.
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http://dx.doi.org/10.1016/j.fertnstert.2007.04.038DOI Listing
April 2008

Repair of infarcted myocardium by an extract of Geum japonicum with dual effects on angiogenesis and myogenesis.

Clin Chem 2006 Aug 22;52(8):1460-8. Epub 2006 Jun 22.

Li Ka Shing Institute of Health Sciences, Department of Medicine, The Chinese University of Hong Kong, Prince of Wales Hospital, Hong Kong SAR.

Background: It has become apparent recently that cardiac myocytes can divide after myocardial infarction, a circumstance that challenges the orthodox view that myocytes may be terminally differentiated. Replacement of the necrosed heart tissue by newly regenerated functional myocardium is a therapeutic ideal, but attempts to reconstitute functional myocardia and coronary vessels have been less successful.

Methods: We isolated a fraction containing 5 compounds from the Chinese herb Geum japonicum, which stimulates the processes of angiogenesis and cardiomyogenesis. We investigated these dual properties in both ex vivo and in vivo systems.

Results: We observed that this bioactive fraction displayed favorable dual actions on early angiogenesis and cardiomyogenesis in acute myocardial infarction in an animal model. Our results demonstrated that application of this bioactive fraction showed pronounced effects on limiting infarct size by 35%-45%, stimulating early development of new blood vessels in 24 h, and regenerating myocardium, replacing approximately 49% of the total infarction volume after 2 weeks. Echocardiographic studies demonstrated marked improvement of left ventricular function within 2 days after infarction, and the improvement was sustained for >1 month.

Conclusions: The properties of this bioactive fraction appear to be entirely novel and represent a new approach for the treatment of ischemic heart disease.
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http://dx.doi.org/10.1373/clinchem.2006.068247DOI Listing
August 2006

Purification and structural characterization of the central hydrophobic domain of oleosin.

J Biol Chem 2002 Oct 17;277(40):37888-95. Epub 2002 Jul 17.

Department of Medicine & Therapeutics, Prince of Wales Hospital, The Chinese University of Hong Kong, Shatin, New Territory, Hong Kong.

The oil bodies of rapeseeds contain a triacylglycerol matrix surrounded by a monolayer of phospholipids embedded with abundant structural alkaline proteins termed oleosins and some other minor proteins. Oleosins are unusual proteins because they contain a 70-80-residue uninterrupted nonpolar domain flanked by relatively polar C- and N-terminal domains. Although the hydrophilic N-terminal domain had been studied, the structural feature of the central hydrophobic domain remains unclear due to its high hydrophobicity. In the present study, we reported the generation, purification, and characterization of a 9-kDa central hydrophobic domain from rapeseed oleosin (19 kDa). The 9-kDa central hydrophobic domain was produced by selectively degrading the N and C termini with enzymes and then purifying the digest by SDS-PAGE and electroelution. We have also reconstituted the central domain into liposomes and synthetic oil bodies to determine the secondary structure of the domain using CD and Fourier transform infrared (FTIR) spectroscopy. The spectra obtained from CD and FTIR were analyzed with reference to structural information of the N-terminal domain and the full-length rapeseed oleosin. Both CD and FTIR analysis revealed that 50-63% of the domain was composed of beta-sheet structure. Detailed analysis of the FTIR spectra indicated that 80% of the beta-sheet structure, present in the central domain, was arranged in parallel to the intermolecular beta-sheet structure. Therefore, interactions between adjacent oleosin proteins would give rise to a stable beta-sheet structure that would extend around the surface of the seed oil bodies stabilizing them in emulsion systems. The strategies used in our present study are significant in that it could be generally used to study difficult proteins with different independent structural domains, especially with long hydrophobic domains.
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http://dx.doi.org/10.1074/jbc.M202721200DOI Listing
October 2002
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