Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis

Takashi Sugimoto; Kazuhisa Ikemoto; Shizuaki Murata; Masahiro Tazawa; Takahide Nomura; Yasumichi Hagino; Hiroshi Ichinose; Toshiharu Nagatsu

doi:10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis

Takashi Sugimoto, Kazuhisa Ikemoto, Shizuaki Murata, Masahiro Tazawa, Takahide Nomura, Yasumichi Hagino, Hiroshi Ichinose, Toshiharu Nagatsu

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

The structure of the native pteridine in Tetrahymena pyriformis was determined as (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3-trihydroxypropyl] pteridin-4(3H)-one; 4). First, the configuration of the 1,2,3-trihydroxypropyl side chain was confirmed as D-threo by the fluorescence-detected circular dichroism (FDCD) spectrum of its aromatic pterin derivative 2 obtained by I₂ oxidation (Fig. 1). The configuration at the 6-position of 4 was determined as (R) by comparison of its hexaacetyl derivative 6 with authentic (6R)- and (6S)-hexaacetyl-5,6,7,8-tetrahydro-D-monapterins 6 and 7, respectively, in the HPLC, LC/MS, and LC-MS/MS (Figs. 3-6). (6R)-5,6,7,8-Tetrahydro-D-monapterin (4) is a newly discovered natural tetrahydropterin.

Original language	English
Pages (from-to)	918-927
Number of pages	10
Journal	Helvetica Chimica Acta
Volume	84
Issue number	4
DOIs	https://doi.org/10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M
Publication status	Published - 2001
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

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Sugimoto, T., Ikemoto, K., Murata, S., Tazawa, M., Nomura, T., Hagino, Y., Ichinose, H., & Nagatsu, T. (2001). Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis. Helvetica Chimica Acta, 84(4), 918-927. https://doi.org/10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

@article{b4608adc6a8648c483f3df56207dfaac,

title = "Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis",

abstract = "The structure of the native pteridine in Tetrahymena pyriformis was determined as (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3-trihydroxypropyl] pteridin-4(3H)-one; 4). First, the configuration of the 1,2,3-trihydroxypropyl side chain was confirmed as D-threo by the fluorescence-detected circular dichroism (FDCD) spectrum of its aromatic pterin derivative 2 obtained by I2 oxidation (Fig. 1). The configuration at the 6-position of 4 was determined as (R) by comparison of its hexaacetyl derivative 6 with authentic (6R)- and (6S)-hexaacetyl-5,6,7,8-tetrahydro-D-monapterins 6 and 7, respectively, in the HPLC, LC/MS, and LC-MS/MS (Figs. 3-6). (6R)-5,6,7,8-Tetrahydro-D-monapterin (4) is a newly discovered natural tetrahydropterin.",

author = "Takashi Sugimoto and Kazuhisa Ikemoto and Shizuaki Murata and Masahiro Tazawa and Takahide Nomura and Yasumichi Hagino and Hiroshi Ichinose and Toshiharu Nagatsu",

year = "2001",

doi = "10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M",

language = "English",

volume = "84",

pages = "918--927",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Verlag Helvetica Chimica Acta AG",

number = "4",

}

Sugimoto, T, Ikemoto, K, Murata, S, Tazawa, M, Nomura, T, Hagino, Y, Ichinose, H & Nagatsu, T 2001, 'Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis', Helvetica Chimica Acta, vol. 84, no. 4, pp. 918-927. https://doi.org/10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis. / Sugimoto, Takashi; Ikemoto, Kazuhisa; Murata, Shizuaki et al.
In: Helvetica Chimica Acta, Vol. 84, No. 4, 2001, p. 918-927.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis

AU - Sugimoto, Takashi

AU - Ikemoto, Kazuhisa

AU - Murata, Shizuaki

AU - Tazawa, Masahiro

AU - Nomura, Takahide

AU - Hagino, Yasumichi

AU - Ichinose, Hiroshi

AU - Nagatsu, Toshiharu

PY - 2001

Y1 - 2001

N2 - The structure of the native pteridine in Tetrahymena pyriformis was determined as (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3-trihydroxypropyl] pteridin-4(3H)-one; 4). First, the configuration of the 1,2,3-trihydroxypropyl side chain was confirmed as D-threo by the fluorescence-detected circular dichroism (FDCD) spectrum of its aromatic pterin derivative 2 obtained by I2 oxidation (Fig. 1). The configuration at the 6-position of 4 was determined as (R) by comparison of its hexaacetyl derivative 6 with authentic (6R)- and (6S)-hexaacetyl-5,6,7,8-tetrahydro-D-monapterins 6 and 7, respectively, in the HPLC, LC/MS, and LC-MS/MS (Figs. 3-6). (6R)-5,6,7,8-Tetrahydro-D-monapterin (4) is a newly discovered natural tetrahydropterin.

AB - The structure of the native pteridine in Tetrahymena pyriformis was determined as (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3-trihydroxypropyl] pteridin-4(3H)-one; 4). First, the configuration of the 1,2,3-trihydroxypropyl side chain was confirmed as D-threo by the fluorescence-detected circular dichroism (FDCD) spectrum of its aromatic pterin derivative 2 obtained by I2 oxidation (Fig. 1). The configuration at the 6-position of 4 was determined as (R) by comparison of its hexaacetyl derivative 6 with authentic (6R)- and (6S)-hexaacetyl-5,6,7,8-tetrahydro-D-monapterins 6 and 7, respectively, in the HPLC, LC/MS, and LC-MS/MS (Figs. 3-6). (6R)-5,6,7,8-Tetrahydro-D-monapterin (4) is a newly discovered natural tetrahydropterin.

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U2 - 10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

DO - 10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

M3 - Article

AN - SCOPUS:0035050265

SN - 0018-019X

VL - 84

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JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 4

ER -

Sugimoto T, Ikemoto K, Murata S, Tazawa M, Nomura T, Hagino Y et al. Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis. Helvetica Chimica Acta. 2001;84(4):918-927. doi: 10.1002/1522-2675(20010418)84:4<918::AID-HLCA918>3.0.CO;2-M

Identification of (6R)-5,6,7,8-tetrahydro-D-monapterin (=(6R)-2-amino-5,6,7,8-tetrahydro-6-[(1R,2R)-1,2,3 -trihydroxypropyl]-pteridin-4(3H)-one) as the native pteridine in Tetrahymena pyriformis

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