Carcinogenesis, Vol. 21, No. 4, 850,
April 2000
© 2000 Oxford University Press
Corrigendum |
Absolute configuration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol formed metabolically from 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
The structures of the enantiomers of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) reported in this paper are reversed. In Figure 2, the correct order of elution should be [S-(Z)]NNAL-(S)-MTPA, [S-(E)]NNAL-(S)-MTPA, [R-(Z)]NNAL-(S)-MTPA, and [R-(E)]NNAL-(S)-MTPA. These were prepared by reaction of racemic NNAL with (R)-(-)MTPA chloride. The correct assignments in Figure 3B and Table I are: entry 1, (S)-NNAL-(S)-MTPA; entry 2, (R)-NNAL-(S)-MTPA; entry 3, (R)-NNAL(R)-MTPA; entry 4, (S)-NNAL-(R)-MTPA. The origin of the mistake is the following: the acid chlorides used in the reactions to prepare the MTPA esters were (R)-(-)-MTPA chloride and (S)-(+)-MTPA chloride, not (S)-(-)-MTPA chloride and (R)-(+)-MTPA chloride as stated in the paper. Because of a quirk of nomenclature, (R)-(-)-MTPA chloride corresponds to (S)-(–)-MTPA as well as (S)-MTPA esters while (S)-(+)-MTPA chloride corresponds to (R)-(+)-MTPA and (R)-MTPA esters. The absolute configuration of 4-hydroxy-4-(3-pyridyl)butanoic acid (hydroxy acid) enantiomers were also assigned based on our original NNAL assignment and therefore are also reversed (1,2). We are aware of three other papers in which the NNAL assignments are reversed (3–5). The authors apologize for the confusion which may have been caused by this error.
References
- Trushin,N. and Hecht,S.S. (1999) Stereoselective metabolism of nicotine and tobacco-specific N-nitrosamines to 4-hydroxy-4-(3-pyridyl)butanoic acid in rats. Chem. Res. Toxicol., 12, 164–171.[ISI][Medline]
- Hecht,S.S., Hatsukami,D.K., Bonilla,L.E. and Hochalter,J.B. (1999) Quantitation of 4-oxo-4-(3-pyridyl)butanoic acid and enantiomers of 4-hydroxy-4-(3-pyridyl)butanoic acid in human urine: a substantial pathway of nicotine metabolism. Chem. Res. Toxicol., 12, 172–179.[ISI][Medline]
-
Upadhyaya,P., Kenney,P.M.J., Hochalter,J.B., Wang,M. and Hecht,S.S. (1999) Tumorigenicity and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) enantiomers and metabolites in the A/J mouse. Carcinogenesis, 20, 1577–1582.
[Abstract/Free Full Text] -
Carmella,S.G., Ye,M., Upadhyaya,P. and Hecht,S.S. (1999) Stereochemistry of metabolites of a tobacco-specific lung carcinogen in smokers' urine. Cancer Res., 59, 3602–3605.
[Abstract/Free Full Text] -
Ren,Q., Murphy,S.E., Dannenberg,A.J., Park,J.Y., Tephly,T.R. and Lazarus,P. (1999) Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by rat UDP-glucuronosyltransferase 2B1. Drug Metab. Dispos., 27, 1010–1016.
[Abstract/Free Full Text]
CiteULike 
Connotea 
Del.icio.us What's this?
This article has been cited by other articles:
|
|
 |
|
  U. Breyer-Pfaff, H.-J. Martin, M. Ernst, and E. Maser ENANTIOSELECTIVITY OF CARBONYL REDUCTION OF 4-METHYLNITROSAMINO-1-(3-PYRIDYL)-1-BUTANONE BY TISSUE FRACTIONS FROM HUMAN AND RAT AND BY ENZYMES ISOLATED FROM HUMAN LIVER Drug Metab. Dispos., September 1, 2004; 32(9): 915 - 922. [Abstract] [Full Text] [PDF]
|
|
|
|
 |
|
 E. M. Leslie, K.-i. Ito, P. Upadhyaya, S. S. Hecht, R. G. Deeley, and S. P. C. Cole Transport of the beta -O-Glucuronide Conjugate of the Tobacco-specific Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by the Multidrug Resistance Protein 1 (MRP1). REQUIREMENT FOR GLUTATHIONE OR A NON-SULFUR-CONTAINING ANALOG J. Biol. Chem., July 20, 2001; 276(30): 27846 - 27854. [Abstract] [Full Text] [PDF]
|
|
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||