The stereochemistry of the hydrogen atoms at C-5′of abscisic acid

R. D. Willows; B. V. Milborrow

doi:10.1016/S0031-9422(00)98057-9

The stereochemistry of the hydrogen atoms at C-5′of abscisic acid

R. D. Willows^*, B. V. Milborrow

^*Corresponding author for this work

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

5 Citations (Scopus)

Abstract

Slices of unripe avocado fruit placed in ²H₂O (45 atom %) synthesized abscisic acid enriched 18.7% with ²H at C-5′. 500 MHz ¹H NMR showed that the signal of the axial, 5′-pro-S H atom was decreased by 20%. The signal of the uncoupled, equatorial H atom was 9 Hz upfield owing to shielding from its geminal²H partner, the reciprocal shielding was 8.9 Hz. The H⁺ added during cyclization, therefore, is at the C-5′-pro-S position of ABA. Unlabelled ABA leaked into the medium, the newly synthesized, ²H labelled ABA was retained in the tissue.

Original language	English
Pages (from-to)	2641-2642
Number of pages	2
Journal	Phytochemistry
Volume	28
Issue number	10
DOIs	https://doi.org/10.1016/S0031-9422(00)98057-9
Publication status	Published - 1989
Externally published	Yes

Keywords

H shielding
abscisic acid
Avocado
biosynthesis
cyclization
NMR.

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10.1016/S0031-9422(00)98057-9

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title = "The stereochemistry of the hydrogen atoms at C-5′of abscisic acid",

abstract = "Slices of unripe avocado fruit placed in 2H2O (45 atom %) synthesized abscisic acid enriched 18.7% with 2H at C-5′. 500 MHz 1H NMR showed that the signal of the axial, 5′-pro-S H atom was decreased by 20%. The signal of the uncoupled, equatorial H atom was 9 Hz upfield owing to shielding from its geminal 2H partner, the reciprocal shielding was 8.9 Hz. The H+ added during cyclization, therefore, is at the C-5′-pro-S position of ABA. Unlabelled ABA leaked into the medium, the newly synthesized, 2H labelled ABA was retained in the tissue.",

keywords = "H shielding, abscisic acid, Avocado, biosynthesis, cyclization, NMR.",

author = "Willows, {R. D.} and Milborrow, {B. V.}",

year = "1989",

doi = "10.1016/S0031-9422(00)98057-9",

language = "English",

volume = "28",

pages = "2641--2642",

journal = "Phytochemistry",

issn = "0031-9422",

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number = "10",

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TY - JOUR

T1 - The stereochemistry of the hydrogen atoms at C-5′of abscisic acid

AU - Willows, R. D.

AU - Milborrow, B. V.

PY - 1989

Y1 - 1989

N2 - Slices of unripe avocado fruit placed in 2H2O (45 atom %) synthesized abscisic acid enriched 18.7% with 2H at C-5′. 500 MHz 1H NMR showed that the signal of the axial, 5′-pro-S H atom was decreased by 20%. The signal of the uncoupled, equatorial H atom was 9 Hz upfield owing to shielding from its geminal 2H partner, the reciprocal shielding was 8.9 Hz. The H+ added during cyclization, therefore, is at the C-5′-pro-S position of ABA. Unlabelled ABA leaked into the medium, the newly synthesized, 2H labelled ABA was retained in the tissue.

AB - Slices of unripe avocado fruit placed in 2H2O (45 atom %) synthesized abscisic acid enriched 18.7% with 2H at C-5′. 500 MHz 1H NMR showed that the signal of the axial, 5′-pro-S H atom was decreased by 20%. The signal of the uncoupled, equatorial H atom was 9 Hz upfield owing to shielding from its geminal 2H partner, the reciprocal shielding was 8.9 Hz. The H+ added during cyclization, therefore, is at the C-5′-pro-S position of ABA. Unlabelled ABA leaked into the medium, the newly synthesized, 2H labelled ABA was retained in the tissue.

KW - H shielding

KW - abscisic acid

KW - Avocado

KW - biosynthesis

KW - cyclization

KW - NMR.

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U2 - 10.1016/S0031-9422(00)98057-9

DO - 10.1016/S0031-9422(00)98057-9

M3 - Article

AN - SCOPUS:38249024809

VL - 28

SP - 2641

EP - 2642

JO - Phytochemistry

JF - Phytochemistry

SN - 0031-9422

IS - 10

ER -

The stereochemistry of the hydrogen atoms at C-5′of abscisic acid

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Keywords

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