D-Tyrosine
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D-Tyrosine

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Category
D-Amino Acids
Catalog number
BAT-003515
CAS number
556-02-5
Molecular Formula
C9H11NO3
Molecular Weight
181.19
D-Tyrosine
IUPAC Name
(2R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Synonyms
D-Tyr-OH; (R)-3-(4-Hydroxyphenyl)alanine; (R)-2-amino-3-(4-hydroxyphenyl)propanoic acid
Appearance
White to off-white powder
Purity
≥ 98% (Titration)
Density
1.2375 g/cm3(rough estimate)
Melting Point
>300 °C
Boiling Point
314.29°C (rough estimate)
Storage
Store at RT
InChI
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m1/s1
InChI Key
OUYCCCASQSFEME-MRVPVSSYSA-N
Canonical SMILES
C1=CC(=CC=C1CC(C(=O)O)N)O
1. D-tyrosine negatively regulates melanin synthesis by competitively inhibiting tyrosinase activity
Jisu Park, Hyejung Jung, Kyuri Kim, Kyung-Min Lim, Ji-Young Kim, Eek-Hoon Jho, Eok-Soo Oh Pigment Cell Melanoma Res. 2018 May;31(3):374-383. doi: 10.1111/pcmr.12668. Epub 2017 Nov 27.
Although L-tyrosine is well known for its melanogenic effect, the contribution of D-tyrosine to melanin synthesis was previously unexplored. Here, we reveal that, unlike L-tyrosine, D-tyrosine dose-dependently reduced the melanin contents of human MNT-1 melanoma cells and primary human melanocytes. In addition, 500 μM of D-tyrosine completely inhibited 10 μM L-tyrosine-induced melanogenesis, and both in vitro assays and L-DOPA staining MNT-1 cells showed that tyrosinase activity is reduced by D-tyrosine treatment. Thus, D-tyrosine appears to inhibit L-tyrosine-mediated melanogenesis by competitively inhibiting tyrosinase activity. Furthermore, we found that D-tyrosine inhibited melanogenesis induced by α-MSH treatment or UV irradiation, which are the most common environmental factors responsible for melanin synthesis. Finally, we confirmed that D-tyrosine reduced melanin synthesis in the epidermal basal layer of a 3D human skin model. Taken together, these data suggest that D-tyrosine negatively regulates melanin synthesis by inhibiting tyrosinase activity in melanocyte-derived cells.
2. D-tyrosine adds an anti-melanogenic effect to cosmetic peptides
Jisu Park, Hyejung Jung, Bohee Jang, Hyun-Kuk Song, Inn-Oc Han, Eok-Soo Oh Sci Rep. 2020 Jan 14;10(1):262. doi: 10.1038/s41598-019-57159-3.
D-tyrosine is known to negatively regulate melanin synthesis by inhibiting tyrosinase activity. Here, we further reveal that peptides containing terminal D-tyrosine can reduce the melanin contents of human melanocytes. The addition of D-tyrosine to the terminus of the commercial anti-wrinkle peptide, pentapeptide-18 endowed the peptide with the ability to reduce the melanin content and tyrosinase activity in human MNT-1 melanoma cells and primary melanocytes. Consistently, terminal D-tyrosine-containing pentapeptide-18 inhibited the melanogenesis induced by α-MSH treatment or UV irradiation of MNT-1 cells and reduced melanin synthesis in the epidermal basal layer of a 3D human skin model. Furthermore, the addition of D-tyrosine to an anti-aging peptide (GEKG) or an anti-inflammatory peptide (GHK) endowed these short peptides with anti-melanogenic effects without altering their intrinsic effects. Together, these data suggest that the addition of D-tyrosine at the terminus of a short cosmetic peptide adds an anti-melanogenic effect to its intrinsic cosmetic effect. Our work offers a novel means of generating dual-function cosmetic peptides.
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