Literature DB >> 3924652

Tyrosinase-catalyzed conjugation of dopa with glutathione.

S Ito, A Palumbo, G Prota.   

Abstract

A convenient method is described for the preparation of 5-S- and 2-S-glutathionyldopa, based on tyrosinase oxidation of dopa in the presence of glutathione. The yields of 5-S, 2-S, and 6-S isomers produced were about 76, 12, and 5%, respectively.

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Year:  1985        PMID： 3924652     DOI： 10.1007/bf01970033

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


  10 in total

1.  Formation of glutathionedopa in albino rats after DOPA injection.

Authors:  C Fehling; C Hansson; J Poulsen; H Rorsman; E Rosengren
Journal:  Acta Derm Venereol       Date:  1981       Impact factor: 4.437

2.  Distribution and metabolism of tritiumlabelled 5-S-cysteinyldopa in mice.

Authors:  S Ito; R Teradaira; K Fujita
Journal:  Biochem Pharmacol       Date:  1980-12       Impact factor: 5.858

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

Authors:  S Ito; G Prota
Journal:  Experientia       Date:  1977-08-15

4.  Role of thiol compounds in mammalian melanin pigmentation. II. Glutathione and related enzymatic activities.

Authors:  J P Benedetto; J P Ortonne; C Voulot; C Khatchadourian; G Prota; J Thivolet
Journal:  J Invest Dermatol       Date:  1982-12       Impact factor: 8.551

5.  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

6.  Synthesis and antitumor activity of cysteinyl-3,4-dihydroxyphenylalanines and related compounds.

Authors:  S Ito; S Inoue; Y Yamamoto; K Fujita
Journal:  J Med Chem       Date:  1981-06       Impact factor: 7.446

7.  Urinary free and conjugated 5-S-cysteinyldopa in normal subjects and in patients with melanoma.

Authors:  V Graef; E Paul
Journal:  Br J Dermatol       Date:  1982-01       Impact factor: 9.302

8.  Glutathionedopa in malignant melanoma.

Authors:  G Agrup; B Falck; H Rorsman; A M Rosengren; E Rosengren
Journal:  Acta Derm Venereol       Date:  1977       Impact factor: 4.437

9.  Characterization of structural properties for morphologic differentiation of melanosomes. III. free and protein-bound dopa and 5-S-cysteinyldopa in B16 and Harding-Passey melanomas.

Authors:  S Ito; K Homma; M Kiyota; K Fujita; K Jimbow
Journal:  J Invest Dermatol       Date:  1983-03       Impact factor: 8.551

10.  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
  10 in total
  7 in total

Review 1.  Continuing to illuminate the mechanisms underlying UV-mediated melanomagenesis.

Authors:  Ryan W Dellinger; Feng Liu-Smith; Frank L Meyskens
Journal:  J Photochem Photobiol B       Date:  2014-06-20       Impact factor: 6.252

2.  Melanosomal damage in normal human melanocytes induced by UVB and metal uptake--a basis for the pro-oxidant state of melanoma.

Authors:  Shirley Gidanian; Mallory Mentelle; Frank L Meyskens; Patrick J Farmer
Journal:  Photochem Photobiol       Date:  2008-03-07       Impact factor: 3.421

3.  Effects of exogenous factors on the cerebral glutathione in rodents.

Authors:  E Bien; K Vick; G Skorka
Journal:  Arch Toxicol       Date:  1992       Impact factor: 5.153

4.  Density Functional Theory-Based Calculation Shed New Light on the Bizarre Addition of Cysteine Thiol to Dopaquinone.

Authors:  Ryo Kishida; Shosuke Ito; Manickam Sugumaran; Ryan Lacdao Arevalo; Hiroshi Nakanishi; Hideaki Kasai
Journal:  Int J Mol Sci       Date:  2021-01-29       Impact factor: 5.923

5.  Disentangling the Puzzling Regiochemistry of Thiol Addition to o-Quinones.

Authors:  Maria L Alfieri; Alice Cariola; Lucia Panzella; Alessandra Napolitano; Marco d'Ischia; Luca Valgimigli; Orlando Crescenzi
Journal:  J Org Chem       Date:  2022-03-10       Impact factor: 4.354

Review 6.  Chemical Reactivities of ortho-Quinones Produced in Living Organisms: Fate of Quinonoid Products Formed by Tyrosinase and Phenoloxidase Action on Phenols and Catechols.

Authors:  Shosuke Ito; Manickam Sugumaran; Kazumasa Wakamatsu
Journal:  Int J Mol Sci       Date:  2020-08-24       Impact factor: 5.923

Review 7.  Metabolic Basis and Clinical Evidence for Skin Lightening Effects of Thiol Compounds.

Authors:  Yong Chool Boo
Journal:  Antioxidants (Basel)       Date:  2022-03-04
  7 in total

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