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Title: Synthesis and characterization of ( sup 3 H)-5 prime azido-N-1-naphthylphthlamic acid, a photolabile N-1-naphthylphthalamic acid analog

Abstract

The NPA (N-1-naphthylphthalamic acid) receptor is an important protein involved in the regulation of transport of indole-3-acetic acid (IAA). In our attempt to isolate and characterize this protein we have previously synthesized and characterized a photolabile analog of NPA, 5{prime}-azido-NPA (Az-NPA) and shown it to be a competitor of NPA for binding sites on the NPA receptor as well as an inhibitor of auxin transport. We have now synthesized and characterized ({sup 3}H)-Az-NPA. The precursor, 2,3,4,5-Br-5{prime}-amino-NPA was dehydrohalogenated with tritium gas by Research Products International. The amino group was converted to an azido group and the product purified by HPLC. ({sup 3}H)-Az-NPA was found to be photolabile and to co-chromatograph with our synthetic unlabeled Az-NPA. Furthermore, the tritiated material was found to bind to zucchini hypocotyl cell membranes in a manner competitive with NPA as well as unlabeled Az-NPA. Photolysis of zucchini phase-partitioned plasma membranes in the presence of ({sup 3}H)-Az-NPA resulted in covalent association of tritium with the membranes. Much of this covalent association could be prevented by prior treatment of the membranes with excess NPA.

Authors:
; ; ; ; ; ; ;  [1]
  1. Swarthmore College, PA (USA)
Publication Date:
OSTI Identifier:
5725366
Report Number(s):
CONF-9007196-
Journal ID: ISSN 0079-2241; CODEN: PPYSA
Resource Type:
Conference
Journal Name:
Plant Physiology, Supplement; (USA)
Additional Journal Information:
Journal Volume: 93:1; Conference: Annual meeting of the American Society of Plant Physiologists, Indianapolis, IN (USA), 29 Jul - 2 Aug 1990; Journal ID: ISSN 0079-2241
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; PROTEINS; BIOSYNTHESIS; ACETIC ACID; CELL MEMBRANES; TRACER TECHNIQUES; TRITIUM COMPOUNDS; VEGETABLES; CARBOXYLIC ACIDS; CELL CONSTITUENTS; FOOD; HYDROGEN COMPOUNDS; ISOTOPE APPLICATIONS; MEMBRANES; MONOCARBOXYLIC ACIDS; ORGANIC ACIDS; ORGANIC COMPOUNDS; PLANTS; SYNTHESIS; 550201* - Biochemistry- Tracer Techniques

Citation Formats

Voet, J G, Dodge, B, Harris, K, Jacobs, M, Larkin, L, Bader, S, Schnitzler, G, and Sutherland, J. Synthesis and characterization of ( sup 3 H)-5 prime azido-N-1-naphthylphthlamic acid, a photolabile N-1-naphthylphthalamic acid analog. United States: N. p., 1990. Web.
Voet, J G, Dodge, B, Harris, K, Jacobs, M, Larkin, L, Bader, S, Schnitzler, G, & Sutherland, J. Synthesis and characterization of ( sup 3 H)-5 prime azido-N-1-naphthylphthlamic acid, a photolabile N-1-naphthylphthalamic acid analog. United States.
Voet, J G, Dodge, B, Harris, K, Jacobs, M, Larkin, L, Bader, S, Schnitzler, G, and Sutherland, J. 1990. "Synthesis and characterization of ( sup 3 H)-5 prime azido-N-1-naphthylphthlamic acid, a photolabile N-1-naphthylphthalamic acid analog". United States.
@article{osti_5725366,
title = {Synthesis and characterization of ( sup 3 H)-5 prime azido-N-1-naphthylphthlamic acid, a photolabile N-1-naphthylphthalamic acid analog},
author = {Voet, J G and Dodge, B and Harris, K and Jacobs, M and Larkin, L and Bader, S and Schnitzler, G and Sutherland, J},
abstractNote = {The NPA (N-1-naphthylphthalamic acid) receptor is an important protein involved in the regulation of transport of indole-3-acetic acid (IAA). In our attempt to isolate and characterize this protein we have previously synthesized and characterized a photolabile analog of NPA, 5{prime}-azido-NPA (Az-NPA) and shown it to be a competitor of NPA for binding sites on the NPA receptor as well as an inhibitor of auxin transport. We have now synthesized and characterized ({sup 3}H)-Az-NPA. The precursor, 2,3,4,5-Br-5{prime}-amino-NPA was dehydrohalogenated with tritium gas by Research Products International. The amino group was converted to an azido group and the product purified by HPLC. ({sup 3}H)-Az-NPA was found to be photolabile and to co-chromatograph with our synthetic unlabeled Az-NPA. Furthermore, the tritiated material was found to bind to zucchini hypocotyl cell membranes in a manner competitive with NPA as well as unlabeled Az-NPA. Photolysis of zucchini phase-partitioned plasma membranes in the presence of ({sup 3}H)-Az-NPA resulted in covalent association of tritium with the membranes. Much of this covalent association could be prevented by prior treatment of the membranes with excess NPA.},
doi = {},
url = {https://www.osti.gov/biblio/5725366}, journal = {Plant Physiology, Supplement; (USA)},
issn = {0079-2241},
number = ,
volume = 93:1,
place = {United States},
year = {Tue May 01 00:00:00 EDT 1990},
month = {Tue May 01 00:00:00 EDT 1990}
}

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