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Literature DB >> 408183

A facile one-step synthesis of cysteinyldopas using mushroom tyrosinase.

Abstract

A convenient one-step procedure, based upon the tyrosinase co-oxidation of dopa and cysteine, is reported for the synthesis of 5-S-cysteinyldopa (I) in 74% yield. Secondary products of the reaction turned out to be 2-S-cysteinyldopa (II, 14%), 2,5-S, S-dicysteinyldopa (iv, 5%), and the hitherto unknown 6-S-cysteinyldopa (III, approximately 1%).

Entities: Chemical Species

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Year: 1977 PMID： 408183 DOI： 10.1007/bf01946005

Source DB: PubMed Journal: Experientia ISSN： 0014-4754

6 in total

1. [Chemical or enzymatic oxidation of 3,4-dihydroxy-L-phenylalanine, hydroxytyramine and noradrenaline studied by paper chromatography and electrophoresis].

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Journal: Bull Soc Chim Biol (Paris) Date: 1960

2. Fluorometry of catechol thioethers.

Authors: H Rorsman; A M Rosengren; E Rosengren
Journal: Acta Derm Venereol Date: 1972 Impact factor: 4.437

3. Melanin pigmentation in mammals.

Authors: G Prota; R H Thomson
Journal: Endeavour Date: 1976-01 Impact factor: 0.444

4. The pigments of reddish hair and feathers.

Authors: R H Thomson
Journal: Angew Chem Int Ed Engl Date: 1974-05 Impact factor: 15.336

5. Urinary excretion of 5-S-cysteinyldopa in patients with primary melanoma or melanoma metastasis.

Authors: G Agrup; P Agrup; T Andersson; B Falck; S Jacobsson; H Rorsman; E Rosengren
Journal: Acta Derm Venereol Date: 1975 Impact factor: 4.437

6. Determination of 5-S-cysteinyldopa in melanomas with a fluorimetric method.

Authors: H Rorsman; A M Rosengren; E Rosengren
Journal: Yale J Biol Med Date: 1973-12

6 in total

20 in total

1. A kinetic study of irreversible enzyme inhibition by an inhibitor that is rendered unstable by enzymic catalysis. The inhibition of polyphenol oxidase by L-cysteine.

Authors: E Valero; R Varón; F García-Carmona
Journal: Biochem J Date: 1991-08-01 Impact factor: 3.857

2. Co-polymerization of dopa and cysteinyldopa in melanogenesis in vitro.

Authors: S Ito; E Novellino; F Chioccara; G Misuraca; G Prota
Journal: Experientia Date: 1980-07-15

3. Quantitative analysis of eumelanin and pheomelanin in human malignant-melanoma tissues.

Authors: T Morishima; E Fukuda
Journal: Arch Dermatol Res Date: 1985 Impact factor: 3.017

4. Coating proteins: structure and cross-linking in fp-1 from the green shell mussel Perna canaliculus.

Authors: Hua Zhao; J Herbert Waite
Journal: Biochemistry Date: 2005-12-06 Impact factor: 3.162

5. Oxidation of tyrosine residues in proteins by tyrosinase. Formation of protein-bonded 3,4-dihydroxyphenylalanine and 5-S-cysteinyl-3,4-dihydroxyphenylalanine.

Authors: S Ito; T Kato; K Shinpo; K Fujita
Journal: Biochem J Date: 1984-09-01 Impact factor: 3.857

6. The effect of cysteine on oxidation of tyrosine, dopa, and cysteinyldopas.

Authors: G Agrup; C Hansson; H Rorsman; E Rosengren
Journal: Arch Dermatol Res Date: 1982 Impact factor: 3.017

7. Tyrosinase-catalyzed conjugation of dopa with glutathione.

Authors: S Ito; A Palumbo; G Prota
Journal: Experientia Date: 1985-07-15

8. Cysteinyldopa isomers and dopa in lesions and urine of Japanese patients with malignant melanoma.

Authors: T Morishima; F Tatsumi; E Fukada; M Saito; M Fujita; N Nagashima; S Hanawa
Journal: Arch Dermatol Res Date: 1983 Impact factor: 3.017

Review 9. Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis.

Authors: Kazumasa Wakamatsu; Jonathan H Zippin; Shosuke Ito
Journal: Pigment Cell Melanoma Res Date: 2021-03-22 Impact factor: 4.693

10. Measurement of Melanin Metabolism in Live Cells by [U-¹³C]-L-Tyrosine Fate Tracing Using Liquid Chromatography-Mass Spectrometry.

Authors: Qiuying Chen; Dalee Zhou; Zalfa Abdel-Malek; Fengli Zhang; Philip S Goff; Elena V Sviderskaya; Kazumasa Wakamatsu; Shosuke Ito; Steven S Gross; Jonathan H Zippin
Journal: J Invest Dermatol Date: 2021-02-05 Impact factor: 7.590