Glycyl-prolyl-hydroxyproline

Glycyl-prolyl-hydroxyproline
Identifiers
  • (2S,4R)-1-[(2S)-1-(2-aminoacetyl)pyrrolidine-2-carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC12H19N3O5
Molar mass285.300 g·mol−1
3D model (JSmol)
  • C1C[C@H](N(C1)C(=O)CN)C(=O)N2C[C@@H](C[C@H]2C(=O)O)O
  • InChI=1S/C12H19N3O5/c13-5-10(17)14-3-1-2-8(14)11(18)15-6-7(16)4-9(15)12(19)20/h7-9,16H,1-6,13H2,(H,19,20)/t7-,8+,9+/m1/s1
  • Key:SZEOBSAZWJLOGY-VGMNWLOBSA-N

Glycyl-prolyl-hydroxyproline (Gly-Pro-Hyp, Tripeptide-29) is a tripeptide that is derived from collagen. Repeating units of Gly-Pro-Hyp form a major part of collagen protein, and Gly-Pro-Hyp can be readily produced by partial hydrolysis of collagen. Along with other collagen-derived small peptides such as the dipeptides Hyp-Gly and Pro-Hyp, Gly-Pro-Hyp is widely used in skincare products and sometimes taken internally as a dietary supplement, as it is readily absorbed into the skin and stimulates collagen synthesis by fibroblasts, which aids wound healing and may help to reduce signs of aging. Dietary supplements marketed as containing "collagen" often actually contain low molecular weight collagen peptides derived from partial hydrolysis of collagen, as they are better absorbed into the body than collagen itself.[1][2][3][4][5][6][7][8]

See also

References

  1. ^ Inoue N, Sugihara F, Wang X (September 2016). "Ingestion of bioactive collagen hydrolysates enhance facial skin moisture and elasticity and reduce facial ageing signs in a randomised double-blind placebo-controlled clinical study". Journal of the Science of Food and Agriculture. 96 (12): 4077–4081. Bibcode:2016JSFA...96.4077I. doi:10.1002/jsfa.7606. PMID 26840887.
  2. ^ Yazaki M, Ito Y, Yamada M, Goulas S, Teramoto S, Nakaya MA, et al. (March 2017). "Oral Ingestion of Collagen Hydrolysate Leads to the Transportation of Highly Concentrated Gly-Pro-Hyp and Its Hydrolyzed Form of Pro-Hyp into the Bloodstream and Skin". Journal of Agricultural and Food Chemistry. 65 (11): 2315–2322. Bibcode:2017JAFC...65.2315Y. doi:10.1021/acs.jafc.6b05679. PMID 28244315.
  3. ^ Kim DU, Chung HC, Choi J, Sakai Y, Lee BY (June 2018). "Oral Intake of Low-Molecular-Weight Collagen Peptide Improves Hydration, Elasticity, and Wrinkling in Human Skin: A Randomized, Double-Blind, Placebo-Controlled Study". Nutrients. 10 (7): 826. doi:10.3390/nu10070826. PMC 6073484. PMID 29949889.
  4. ^ Chae M, Bae IH, Lim SH, Jung K, Roh J, Kim W (April 2021). "AP Collagen Peptides Prevent Cortisol-Induced Decrease of Collagen Type I in Human Dermal Fibroblasts". International Journal of Molecular Sciences. 22 (9): 4788. doi:10.3390/ijms22094788. PMC 8125628. PMID 33946465.
  5. ^ Chae M, Moon CY, Lim SH, Yamashita Y, Yamada H, Ide M, et al. (May 2023). "Oral Ingestion of AP Collagen Peptide Leads to Systemic Absorption of Gly-Pro-Hyp, Alleviating H2O2-Induced Dermal Fibroblast Aging". Journal of Medicinal Food. 26 (5): 299–306. doi:10.1089/jmf.2022.K.0149. PMID 37074675.
  6. ^ Yang D, Liu Q, Xu Q, Zheng L, Zhang S, Lu S, et al. (March 2024). "Effects of collagen hydrolysates on UV-induced photoaging mice: Gly-Pro-Hyp as a potent anti-photoaging peptide". Food & Function. 15 (6): 3008–3022. doi:10.1039/d3fo04949c. PMID 38411396.
  7. ^ Oztug M (May 2024). "Bioactive Peptide Profiling in Collagen Hydrolysates: Comparative Analysis Using Targeted and Untargeted Liquid Chromatography-Tandem Mass Spectrometry Quantification". Molecules. 29 (11): 2592. doi:10.3390/molecules29112592. PMC 11173644. PMID 38893467.
  8. ^ Kim CE, Lee JS, Kim YH, Shin YC, Shin SK, Kwon EY (December 2025). "Effects of collagen tripeptide supplementation on oxidative stress and mitochondrial function in aging". Nutrition Research and Practice. 19 (6): 867–879. doi:10.4162/nrp.2025.19.6.867. PMC 12688003. PMID 41377595.
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