Giichi Goto

Leukotriene a: Stereochemistry and enzymatic conversion to leukotriene B

Abstract Leukotriene A was assigned the structure 5(S)- trans -5,6-oxido-7,9- trans -11,14- cis -eicosatetraenoic acid by the enzymatic conversion of a synthetic product of known stereochemistry into the naturally occurring isomer of 5(S),12(R)-dihydroxy-6,8,10,14-eicosatetraenoic acid in human polymorphonuclear leukocytes.

Stereochemistry of leukotriene C-1

Abstract Leukotriene C-1, a “Slow Reacting Substance” (SRS), has been shown to possess the molecular Structure depicted by V (5(S)-hydroxy-6(R)- S -glutathionyl-7,9- trans -11,14- cis -eicosatetraenoic acid) by its identity with a totally synthetic product of known structure and stereochemistry.

Total synthesis of slow reacting substances (SRS). “Leukotriene C-2” (11-trans-leukotriene C) (3) and leukotriene D (4)

Abstract Syntheses are described for the “slow reacting substances” 11- trans -leukotriene C (3) (previously known as leukotriene C-2) and leukotriene D (4), the cys-gly analog of leukotriene C (2). The synthesized leukotrienes 3 and 4 were instrumental in the assignment of structure to these members of the family of naturally occuring slow reacting substances which includes also 2.

Total synthesis of slow reacting substances (SRS's): 6-epi-leukotriene C and 6-epi-leukotriene D

Abstract 6- Epi -leukotrienes C and D (3 and 4) have been synthesized unambiguously via the 5( S ), 6( R )-epoxide (5,6- cis ) which is isomeric with leukotriene A. These 6- epi -leukotrienes are less active (especially 4) than leukotrienes C and D (1 and 2) and have not been found in substantial quantity in natural SRS sources.

11-Trans leukotriene C: A naturally occurring slow reacting substance

Abstract A slow reacting substance, produced by murine mastocytoma cells, has been shown to have the structure 5(S)-hydroxy-6(R)- S -glutathionyl-7,9,11- trans -14- cis -eicosatetraenoic acid (11- trans leukotriene C, previously referred to as leukotriene C-2) by ultraviolet spectroscopy, amino acid analyses, lipoxygenase conversion and comparisions with a synthetic compound of known structure and stereochemistry.