Isomeric Monoacetylmono(1-hydroxyethyl)deuteroporphyrins: Syntheses, Characterization, and Use for the Syntheses of Regioselectively Methyl-and Vinyl-Deuterated Hemins

Fuu Yau Shiau; Kevin M. Smith; Ravindra K. Pandey; Thomas J. Dougherty; S. Ramaprasad

doi:10.1021/jo00294a039

Isomeric Monoacetylmono(1-hydroxyethyl)deuteroporphyrins: Syntheses, Characterization, and Use for the Syntheses of Regioselectively Methyl-and Vinyl-Deuterated Hemins

Fuu Yau Shiau
, Kevin M. Smith
, Ravindra K. Pandey
, Thomas J. Dougherty
, S. Ramaprasad

Institute for Lasers Photonics and Biophotonics

University of California at Davis
University of Arkansas for Medical Sciences
Roswell Park Cancer Institute

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

18 Scopus citations

Abstract

Treatment of hematoporphyrin IX dimethyl ester (7) with tetrapropylammonium perruthenate (Prⁿ₄N)(Ru0₄) and N-methylmorpholine N-oxide affords a high yield of the separable monoacetylmono(1-hydroxyethyl)-deuteroporphyrin isomers 5 and 6. Proton NMR NOE experiments and chemical transformations involving specific individual deuteration at the 1- and 3-methyls and 2- and 4-vinyls are used to characterize the isomers.

Original language	English
Pages (from-to)	2190-2195
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	55
Issue number	7
DOIs	https://doi.org/10.1021/jo00294a039
State	Published - 1990

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title = "Isomeric Monoacetylmono(1-hydroxyethyl)deuteroporphyrins: Syntheses, Characterization, and Use for the Syntheses of Regioselectively Methyl-and Vinyl-Deuterated Hemins",

abstract = "Treatment of hematoporphyrin IX dimethyl ester (7) with tetrapropylammonium perruthenate (Prn4N)(Ru04) and N-methylmorpholine N-oxide affords a high yield of the separable monoacetylmono(1-hydroxyethyl)-deuteroporphyrin isomers 5 and 6. Proton NMR NOE experiments and chemical transformations involving specific individual deuteration at the 1- and 3-methyls and 2- and 4-vinyls are used to characterize the isomers.",

author = "Shiau, \{Fuu Yau\} and Smith, \{Kevin M.\} and Pandey, \{Ravindra K.\} and Dougherty, \{Thomas J.\} and S. Ramaprasad",

year = "1990",

doi = "10.1021/jo00294a039",

language = "English",

volume = "55",

pages = "2190--2195",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "7",

}

TY - JOUR

T1 - Isomeric Monoacetylmono(1-hydroxyethyl)deuteroporphyrins

T2 - Syntheses, Characterization, and Use for the Syntheses of Regioselectively Methyl-and Vinyl-Deuterated Hemins

AU - Shiau, Fuu Yau

AU - Smith, Kevin M.

AU - Pandey, Ravindra K.

AU - Dougherty, Thomas J.

AU - Ramaprasad, S.

PY - 1990

Y1 - 1990

N2 - Treatment of hematoporphyrin IX dimethyl ester (7) with tetrapropylammonium perruthenate (Prn4N)(Ru04) and N-methylmorpholine N-oxide affords a high yield of the separable monoacetylmono(1-hydroxyethyl)-deuteroporphyrin isomers 5 and 6. Proton NMR NOE experiments and chemical transformations involving specific individual deuteration at the 1- and 3-methyls and 2- and 4-vinyls are used to characterize the isomers.

AB - Treatment of hematoporphyrin IX dimethyl ester (7) with tetrapropylammonium perruthenate (Prn4N)(Ru04) and N-methylmorpholine N-oxide affords a high yield of the separable monoacetylmono(1-hydroxyethyl)-deuteroporphyrin isomers 5 and 6. Proton NMR NOE experiments and chemical transformations involving specific individual deuteration at the 1- and 3-methyls and 2- and 4-vinyls are used to characterize the isomers.

UR - https://www.scopus.com/pages/publications/0025148907

U2 - 10.1021/jo00294a039

DO - 10.1021/jo00294a039

M3 - Article

AN - SCOPUS:0025148907

SN - 0022-3263

VL - 55

SP - 2190

EP - 2195

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 7

ER -

Isomeric Monoacetylmono(1-hydroxyethyl)deuteroporphyrins: Syntheses, Characterization, and Use for the Syntheses of Regioselectively Methyl-and Vinyl-Deuterated Hemins

Abstract

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