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39.4.2.1.2.2.4 Variation 4: Biological Oxidation

DOI: 10.1055/sos-SD-039-00359

García Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J.Science of Synthesis, (200839330.

For more than 50 years it has been known that enzymes are able to stereoselectively oxidize sulfides to the corresponding sulfoxides.[‌530‌‌532‌] The fact that the reactions are carried out in water as the solvent and using air as the oxidant makes this approach environmentally friendly and most appealing for industrial applications. Nevertheless, most of the investigated sulfides are not functionalized and the majority of the studies have been performed on alkyl aryl sulfides, which are not included in this section. Two major groups of enzymes have been used in the oxidation of dialkyl sulfides: peroxidases and monooxygenases. The main drawbacks of these methods are related to the need to use special equipment, the purification of the enzyme, and sometimes the tedious procedure for regenerating the expensive cofactor [e.g., flavin adenine dinucleotide (FAD) or nicotinamide adenine dinucleotide (NADP+)].

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Mee eee ee-eeeeeee eeeeeee eee e eeeee eeeee ee eee eeeeeeeee eeeeeeeee ee eeeee eeeeee eeeeeeee ee Meeeeeeeeee eeeeeeeeee eeeeeeeeeeeee (MMM), eeeee eeeeeeeeeeeeeeeee eeeeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeee eeeeeeee eeeeee ee eee eee ee eee eeeee, ee ee eee eeee eee eeeeee eeeeeeee (eeeeee-eeeeeeeeeee eeeeeeee eeeeeeee eee eeee eeeeeeeeeee eeeeeeee) (Meeee 88).[‌888‌]

Meeee 88 Meeeeeeee ee Meeee Meeeee Meeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeee ­eeeeeeeeee Meeeeeeeeeeee[‌888‌]

M8 ee (%) (Meeeee) Mee
eMe 88 (M) [‌888‌]
Me 88 (M) [‌888‌]
(MM8)8Me 88 (M) [‌888‌]
(MM8)8Me 88 (M) [‌888‌]
(MM8)8Me 88 (M) [‌888‌]
(MM8)8Me 88 (M) [‌888‌]
(M)-(MM8)8MM=MMMe 88 (M) [‌888‌]
(M)-(MM8)8MM=MMMe 88 (M) [‌888‌]
(M)-MM8MM=MMMe 8 (M) [‌888‌]
MMMe(MM8)8Me 88 (M) [‌888‌]
(MM8)8Me 88 (M) [‌888‌]
(MM8)8M(MM8)8Me 88 (M) [‌888‌]

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Meeeee 888 Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeeeee Meeeeeeeeeeee[‌888‌]

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Meeee 88 Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeeeee ­eeeeeeeeee[‌888‌]

M8 M8 ee (%) (Meeeee) Meeee (%) Mee
(MM8)8Me (MM8)8MM8Me 88 (M) 8 [‌888‌]
(MM8)8Me (MM8)8MM8Me 88 (M) 8 [‌888‌]
Me (MM8)8MM8Me >88 (M) 88 [‌888‌]

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Meeee 88 Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeee eeeeee MMMMM 88888[‌888‌]

M8 8,8-Meeeeeeeeeeee 8,8-Meeeeeeeeeeee 8,8-Meeeeeeeeeeee 8,8-Meeeeeeeeeeee Mee
ee (%) (Meeeee) Meeee (%) ee (%) (Meeeee) Meeee (%)
(MM8)8Me 88 (M) 88 8 (e) 88 [‌888‌]
(MM8)8Me 88 (M) 88 88 (M) 88 [‌888‌]
(MM8)8Me 88 (M) 88 88 (M) 88 [‌888‌]
(MM8)8Me 8 (M) 8 8 (M) 8 [‌888‌]

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Meeee M8 Meeeeeee Meeeee ee (%) (Meeeee) Meeee (%) Mee
8 (MM8)8Me eeeeeeeeeee eeeeeeeeeee 88 (M) 88 [‌888‌]
8 Me eeeeeeeeeee eeeeeeeeeee 88 (M) 88 [‌888‌]
8 e-Me eeeeeeee eeeeeeeeeeeee eeeeeeeeeeeee 88 (M) 88 [‌888‌]
8 Me eeeeeeee eeeeeeeeeeeee eeeeeeeeeeeee 88 (M) 88 [‌888‌]
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8 e-Me eeeeeeeeeeeee eeeeeeeeeeeee 88 (M) 88 [‌888‌]

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Meeee 88 Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee Meeeeeeeee Meeee Meeeeeeeeeeeeeee eee. MMMM 8888[‌888‌]

M8 ee (%) (Meeeee) Meeee (%) Mee
88 (M) 88 [‌888‌]
eeeeeeeeeee 88 (M) 88 [‌888‌]
8-eeeeeeeeeeeee 88 (M) 88 [‌888‌]
8-eeeeeeeeeeeee 88 (M) 88 [‌888‌]
8-eeeeeeeeeeeee >88 (M) 88 [‌888‌]
Me 88 (M) 88e [‌888‌]

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Meeeee 888 Meeeeeeee ee Meeeeeeeee eee Meeeeeee Meeeeeeeee ee Meeeeeeeee Meeeeeeee[‌888‌,‌888‌]

Mee eeeeeeeeeeeeeeee eeeeeeeee ee e eeee eeeee eeee eee eeeeeeeee eee ee eeeeeeee eeeee eeeee'e eeeee (Meeeeeeeeeeee eeeeeeeeee MMM 8888) eeeee eeeeeee eeeeeeeeee, eeee eeee eeeeeeeeeeee eeeeee eeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee Meeeeeeee Meeee Meeeeeeeeeeee eeeeeeeeee MMM 8888[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee Meeeee Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

Mee eeeeeee (8.8eeee) eee eeeeeeeeeeeeeeee (8 × 888 eeee) eeee eeeeeeeeeeee eeeeeee ee ee eeeeeee eM 8 eeeeee eeee (88eM) ee 8°M eee 8eee. Mee eeeeeee (8eeee) ee eM 8 eeeeee eeee (8eM) eee eeee eeeee eeee 8.8e. Mee eeeeeee eee eeee eeeee eeeeeeee ee 8°M eee eee eeeeeeeeeee eeee eee eee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM. Meeeeeeeee eeee Me8M (8 × 88eM) eee eeee eeee MMMe8 (8 × 88eM), eeeeeeeeeee ee eee eeeeeee eeeee, eee eeeeee eeee eee eeeee eeeeeee. Meee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/MeMM); eeeee: 8888%; 8888% ee.

Meeee Meeeee Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

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References