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Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents.

Journal of the American Chemical Society

Ohshiro H, Mitsui K, Ando N, Ohsawa Y, Koinuma W, Takahashi H, Kondo SI, Nabeshima T, Yano Y.
PMID: 11456915
J Am Chem Soc. 2001 Mar 21;123(11):2478-86. doi: 10.1021/ja0009121.

The oxidizing ability of benzo-dipteridine bearing a bipyridin-6-ylmethyl moiety (4) was found to be increased with Zn(2+) by approximately 10(3)-fold for sulfite addition in MeOH and approximately 10(2)-fold for oxidation of an NADH model in MeCN. It was found...

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Ohshiro H, Mitsui K, Ando N, et al. Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents. J Am Chem Soc. 2001;123(11):2478-86doi: 10.1021/ja0009121.
Ohshiro, H., Mitsui, K., Ando, N., Ohsawa, Y., Koinuma, W., Takahashi, H., Kondo, S. I., Nabeshima, T., & Yano, Y. (2001). Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents. Journal of the American Chemical Society, 123(11), 2478-86. https://doi.org/10.1021/ja0009121
Ohshiro, H, et al. "Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents." Journal of the American Chemical Society vol. 123,11 (2001): 2478-86. doi: https://doi.org/10.1021/ja0009121
Ohshiro H, Mitsui K, Ando N, Ohsawa Y, Koinuma W, Takahashi H, Kondo SI, Nabeshima T, Yano Y. Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents. J Am Chem Soc. 2001 Mar 21;123(11):2478-86. doi: 10.1021/ja0009121. PMID: 11456915.
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Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography.

Chirality

Ding J, Zhang M, Dai H, Lin C.
PMID: 30238493
Chirality. 2018 Dec;30(12):1245-1256. doi: 10.1002/chir.23018. Epub 2018 Sep 20.

Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2-chloromandelic acid, 3-chloromandelic acid, 4-chloromandelic acid, 4-bromomandelic acid,...

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Ding J, Zhang M, Dai H, et al. Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography. Chirality. 2018;30(12):1245-1256doi: 10.1002/chir.23018.
Ding, J., Zhang, M., Dai, H., & Lin, C. (2018). Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography. Chirality, 30(12), 1245-1256. https://doi.org/10.1002/chir.23018
Ding, Jiawei, et al. "Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography." Chirality vol. 30,12 (2018): 1245-1256. doi: https://doi.org/10.1002/chir.23018
Ding J, Zhang M, Dai H, Lin C. Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography. Chirality. 2018 Dec;30(12):1245-1256. doi: 10.1002/chir.23018. Epub 2018 Sep 20. PMID: 30238493.
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Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase.

Journal of separation science

Kacprzak K, Maier N, Lindner W.
PMID: 20715146
J Sep Sci. 2010 Sep;33(17):2590-8. doi: 10.1002/jssc.201000393.

Replacement of the flexible thioether linker for the novel, rigid 1,2,3-triazole spacer group in the course of immobilization of quinine tert-butyl carbamate onto a silica surface led to a chiral stationary phase (CSP) with enhanced enantioselectivity for the resolution...

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Kacprzak K, Maier N, Lindner W. Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. J Sep Sci. 2010;33(17):2590-8doi: 10.1002/jssc.201000393.
Kacprzak, K., Maier, N., & Lindner, W. (2010). Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. Journal of separation science, 33(17), 2590-8. https://doi.org/10.1002/jssc.201000393
Kacprzak, Karol, et al. "Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase." Journal of separation science vol. 33,17 (2010): 2590-8. doi: https://doi.org/10.1002/jssc.201000393
Kacprzak K, Maier N, Lindner W. Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3-triazolo-linked quinine tert-butyl carbamate anion exchange-type chiral stationary phase. J Sep Sci. 2010 Sep;33(17):2590-8. doi: 10.1002/jssc.201000393. PMID: 20715146.
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[Enantioseparation of mandelic acid compounds with Chiralpak AD-H and chiralcel OJ-H chiral stationary phases].

Se pu = Chinese journal of chromatography

Wang M.
PMID: 24822458
Se Pu. 2014 Feb;32(2):198-203. doi: 10.3724/sp.j.1123.2013.09051.

Eight mandelic acid compounds were enantioseparated with amylose-based chiral stationary phase Chiralcel OJ-H and cellulose-based chiral stationary phase Chiralpak AD-H, in the normal-phase mode. It showed that Chiralcel OJ-H exhibited higher enantioseparation, and the eight mandelic acid compounds can...

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Wang M. [Enantioseparation of mandelic acid compounds with Chiralpak AD-H and chiralcel OJ-H chiral stationary phases]. Se Pu. 2014;32(2):198-203doi: 10.3724/sp.j.1123.2013.09051.
Wang, M. (2014). [Enantioseparation of mandelic acid compounds with Chiralpak AD-H and chiralcel OJ-H chiral stationary phases]. Se pu = Chinese journal of chromatography, 32(2), 198-203. https://doi.org/10.3724/sp.j.1123.2013.09051
Wang, Min. "[Enantioseparation of mandelic acid compounds with Chiralpak AD-H and chiralcel OJ-H chiral stationary phases]." Se pu = Chinese journal of chromatography vol. 32,2 (2014): 198-203. doi: https://doi.org/10.3724/sp.j.1123.2013.09051
Wang M. [Enantioseparation of mandelic acid compounds with Chiralpak AD-H and chiralcel OJ-H chiral stationary phases]. Se Pu. 2014 Feb;32(2):198-203. doi: 10.3724/sp.j.1123.2013.09051. Chinese. PMID: 24822458.
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A configurationally stable alkoxy allenyl zinc reagent, en route to anti-anti vicinal amino diols.

Organic letters

Poisson JF, Normant JF.
PMID: 11405737
Org Lett. 2001 Jun 14;3(12):1889-91. doi: 10.1021/ol015941a.

[see reaction]. The reaction of an alkoxyallenyl zinc reagent with benzyl imines derived from lactic and mandelic acids proceeds highly diastereoselectively and leads to 2-amino-1,3-diol derivatives with an anti-anti pattern.

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Poisson JF, Normant JF. A configurationally stable alkoxy allenyl zinc reagent, en route to anti-anti vicinal amino diols. Org Lett. 2001;3(12):1889-91doi: 10.1021/ol015941a.
Poisson, J. F., & Normant, J. F. (2001). A configurationally stable alkoxy allenyl zinc reagent, en route to anti-anti vicinal amino diols. Organic letters, 3(12), 1889-91. https://doi.org/10.1021/ol015941a
Poisson, J F, and Normant, J F. "A configurationally stable alkoxy allenyl zinc reagent, en route to anti-anti vicinal amino diols." Organic letters vol. 3,12 (2001): 1889-91. doi: https://doi.org/10.1021/ol015941a
Poisson JF, Normant JF. A configurationally stable alkoxy allenyl zinc reagent, en route to anti-anti vicinal amino diols. Org Lett. 2001 Jun 14;3(12):1889-91. doi: 10.1021/ol015941a. PMID: 11405737.
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Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids.

The Journal of organic chemistry

Chi L, Zhao J, James TD.
PMID: 18507445
J Org Chem. 2008 Jun 20;73(12):4684-7. doi: 10.1021/jo8007622. Epub 2008 May 29.

New mono boronic acid was found to be an enantioselective fluorescent chemosensor for mono alpha-hydroxyl carboxylic acids, such as mandelic acid and lactic acid. The chiral sensor shows lower background fluorescence, higher fluorescence enhancement, and enantioselective recognition kinetics toward...

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Chi L, Zhao J, James TD. Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids. J Org Chem. 2008;73(12):4684-7doi: 10.1021/jo8007622.
Chi, L., Zhao, J., & James, T. D. (2008). Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids. The Journal of organic chemistry, 73(12), 4684-7. https://doi.org/10.1021/jo8007622
Chi, Lina, et al. "Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids." The Journal of organic chemistry vol. 73,12 (2008): 4684-7. doi: https://doi.org/10.1021/jo8007622
Chi L, Zhao J, James TD. Chiral mono boronic acid as fluorescent enantioselective sensor for mono alpha-hydroxyl carboxylic acids. J Org Chem. 2008 Jun 20;73(12):4684-7. doi: 10.1021/jo8007622. Epub 2008 May 29. PMID: 18507445.
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Application and comparison of high-speed countercurrent chromatography and high performance liquid chromatography in preparative enantioseparation of α-substitution mandelic acids.

Separation science and technology

Tong S, Zhang H, Shen M, Ito Y, Yan J.
PMID: 25983356
Sep Sci Technol. 2015 Apr 01;50(5):735-743. doi: 10.1080/01496395.2014.959602.

Preparative enantioseparations of α-cyclopentylmandelic acid and α-methylmandelic acid by high-speed countercurrent chromatography (HSCCC) and high performance liquid chromatography (HPLC) were compared using hydroxypropy-β-cyclodextrin (HP-β-CD) and sulfobutyl ether-β-cyclodextrin (SBE-β-CD) as the chiral mobile phase additives. In preparative HPLC the enantioseparation...

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Tong S, Zhang H, Shen M, et al. Application and comparison of high-speed countercurrent chromatography and high performance liquid chromatography in preparative enantioseparation of α-substitution mandelic acids. Sep Sci Technol. 2015;50(5):735-743doi: 10.1080/01496395.2014.959602.
Tong, S., Zhang, H., Shen, M., Ito, Y., & Yan, J. (2015). Application and comparison of high-speed countercurrent chromatography and high performance liquid chromatography in preparative enantioseparation of α-substitution mandelic acids. Separation science and technology, 50(5), 735-743. https://doi.org/10.1080/01496395.2014.959602
Tong, Shengqiang, et al. "Application and comparison of high-speed countercurrent chromatography and high performance liquid chromatography in preparative enantioseparation of α-substitution mandelic acids." Separation science and technology vol. 50,5 (2015): 735-743. doi: https://doi.org/10.1080/01496395.2014.959602
Tong S, Zhang H, Shen M, Ito Y, Yan J. Application and comparison of high-speed countercurrent chromatography and high performance liquid chromatography in preparative enantioseparation of α-substitution mandelic acids. Sep Sci Technol. 2015 Apr 01;50(5):735-743. doi: 10.1080/01496395.2014.959602. PMID: 25983356; PMCID: PMC4428595.
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Enantiomeric and mesomeric mandelate complexes of molybdenum -- on their stereospecific formations and absolute configurations.

Journal of inorganic biochemistry

Zhou ZH, Zhao H, Tsai KR.
PMID: 15522406
J Inorg Biochem. 2004 Nov;98(11):1787-94. doi: 10.1016/j.jinorgbio.2004.08.003.

The stereospecific formation and absolute configuration of R-homocitrate coordinated FeMo-co in nitrogenase was mimicked through the structural analyses of a collection of enantiomeric and mesomeric mandelato molybdenum complexes, i.e., (NH(4))(2)[Mo(Delta)O(2)(R-mand)(2)]x3H(2)O (1a), (NH(4))(2)[Mo(Lambda)O(2)(S-mand)(2)]x3H(2)O (1b), (NH(4))(4)[Mo(Delta)O(2)(RS-mand)(2)][Mo(Lambda)O(2)(RS-mand)(2)]x8H(2)O (2), (NH(4))(2)[W(Delta)O(2)(R-mand)(2)]x2H(2)O (3a), (NH(4))(2)[W(Lambda)O(2)(S-mand)(2)]x2H(2)O (3b)...

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Zhou ZH, Zhao H, Tsai KR. Enantiomeric and mesomeric mandelate complexes of molybdenum -- on their stereospecific formations and absolute configurations. J Inorg Biochem. 2004;98(11):1787-94doi: 10.1016/j.jinorgbio.2004.08.003.
Zhou, Z. H., Zhao, H., & Tsai, K. R. (2004). Enantiomeric and mesomeric mandelate complexes of molybdenum -- on their stereospecific formations and absolute configurations. Journal of inorganic biochemistry, 98(11), 1787-94. https://doi.org/10.1016/j.jinorgbio.2004.08.003
Zhou, Zhao-Hui, et al. "Enantiomeric and mesomeric mandelate complexes of molybdenum -- on their stereospecific formations and absolute configurations." Journal of inorganic biochemistry vol. 98,11 (2004): 1787-94. doi: https://doi.org/10.1016/j.jinorgbio.2004.08.003
Zhou ZH, Zhao H, Tsai KR. Enantiomeric and mesomeric mandelate complexes of molybdenum -- on their stereospecific formations and absolute configurations. J Inorg Biochem. 2004 Nov;98(11):1787-94. doi: 10.1016/j.jinorgbio.2004.08.003. PMID: 15522406.
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Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers.

International journal of occupational and environmental health

Cai SX, Ikeda M, Inoue O, Jin C, Kudo S, Liu SJ, Nakatsuka H, Seiji K, Watanabe T.
PMID: 9990150
Int J Occup Environ Health. 1995 Jan;1(1):1-8. doi: 10.1179/oeh.1995.1.1.1.

Factory surveys were conducted in the second half of work weeks on 360 solvent workers (202 men and 158 women) and 281 controls in China. Monitoring personal exposures showed that ethylbenzene exposure was low (geometric mean 1.8 ppm) and...

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Cai SX, Ikeda M, Inoue O, et al. Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers. Int J Occup Environ Health. 1995;1(1):1-8doi: 10.1179/oeh.1995.1.1.1.
Cai, S. X., Ikeda, M., Inoue, O., Jin, C., Kudo, S., Liu, S. J., Nakatsuka, H., Seiji, K., & Watanabe, T. (1995). Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers. International journal of occupational and environmental health, 1(1), 1-8. https://doi.org/10.1179/oeh.1995.1.1.1
Cai, et al. "Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers." International journal of occupational and environmental health vol. 1,1 (1995): 1-8. doi: https://doi.org/10.1179/oeh.1995.1.1.1
Cai SX, Ikeda M, Inoue O, Jin C, Kudo S, Liu SJ, Nakatsuka H, Seiji K, Watanabe T. Urinary Phenylglyoxylic Acid Excretion after Exposure to Ethylbenzene among Solvent-exposed Chinese Workers. Int J Occup Environ Health. 1995 Jan;1(1):1-8. doi: 10.1179/oeh.1995.1.1.1. PMID: 9990150.
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Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot.

Analytical and bioanalytical chemistry

Bai LH, Chen XX, Huang YP, Zhang QW, Liu ZS.
PMID: 24005602
Anal Bioanal Chem. 2013 Nov;405(27):8935-43. doi: 10.1007/s00216-013-7304-4. Epub 2013 Sep 05.

A new chiral stationary phase based on molecularly imprinted polymers (MIP) was prepared in ionic liquid by use of the metal pivot concept. Imprinted monoliths were synthesized by use of a mixture of R-mandelic acid (template), 4-vinylpyridine, ethylene glycol...

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Bai LH, Chen XX, Huang YP, et al. Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot. Anal Bioanal Chem. 2013;405(27):8935-43doi: 10.1007/s00216-013-7304-4.
Bai, L. H., Chen, X. X., Huang, Y. P., Zhang, Q. W., & Liu, Z. S. (2013). Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot. Analytical and bioanalytical chemistry, 405(27), 8935-43. https://doi.org/10.1007/s00216-013-7304-4
Bai, Li-Hong, et al. "Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot." Analytical and bioanalytical chemistry vol. 405,27 (2013): 8935-43. doi: https://doi.org/10.1007/s00216-013-7304-4
Bai LH, Chen XX, Huang YP, Zhang QW, Liu ZS. Chiral separation of racemic mandelic acids by use of an ionic liquid-mediated imprinted monolith with a metal ion as self-assembly pivot. Anal Bioanal Chem. 2013 Nov;405(27):8935-43. doi: 10.1007/s00216-013-7304-4. Epub 2013 Sep 05. PMID: 24005602.
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Controlled .

Organic letters

Muthuraja P, Usman R, Sajeev R, Gopinath P.
PMID: 34279109
Org Lett. 2021 Aug 06;23(15):6014-6018. doi: 10.1021/acs.orglett.1c02080. Epub 2021 Jul 19.

Mandelic acids represent a key structural motif present in many drug molecules. Herein, we report the controlled

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Muthuraja P, Usman R, Sajeev R, et al. Controlled . Org Lett. 2021;23(15):6014-6018doi: 10.1021/acs.orglett.1c02080.
Muthuraja, P., Usman, R., Sajeev, R., & Gopinath, P. (2021). Controlled . Organic letters, 23(15), 6014-6018. https://doi.org/10.1021/acs.orglett.1c02080
Muthuraja, Perumal, et al. "Controlled ." Organic letters vol. 23,15 (2021): 6014-6018. doi: https://doi.org/10.1021/acs.orglett.1c02080
Muthuraja P, Usman R, Sajeev R, Gopinath P. Controlled . Org Lett. 2021 Aug 06;23(15):6014-6018. doi: 10.1021/acs.orglett.1c02080. Epub 2021 Jul 19. PMID: 34279109.
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Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton.

Chemical communications (Cambridge, England)

Chen L, Li H, Yu F, Wang L.
PMID: 25325084
Chem Commun (Camb). 2014 Dec 07;50(94):14866-9. doi: 10.1039/c4cc06331g.

A new protocol for Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates was established, which allows efficient construction of the phthalide skeleton. Interestingly, this reaction underwent a decarboxylative process, in which only divinylation was observed, and the subsequent cyclization...

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Chen L, Li H, Yu F, et al. Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton. Chem Commun (Camb). 2014;50(94):14866-9doi: 10.1039/c4cc06331g.
Chen, L., Li, H., Yu, F., & Wang, L. (2014). Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton. Chemical communications (Cambridge, England), 50(94), 14866-9. https://doi.org/10.1039/c4cc06331g
Chen, Lili, et al. "Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton." Chemical communications (Cambridge, England) vol. 50,94 (2014): 14866-9. doi: https://doi.org/10.1039/c4cc06331g
Chen L, Li H, Yu F, Wang L. Ru-catalyzed decarboxylative cyclization of mandelic acids with acrylates: facile access to the phthalide skeleton. Chem Commun (Camb). 2014 Dec 07;50(94):14866-9. doi: 10.1039/c4cc06331g. PMID: 25325084.
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Showing 1 to 12 of 12 entries