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    Tryptophan
    Information
    CAS No. 54-12-6 Price
    Catalog No.CFN90473Purity>=98%
    Molecular Weight204.22Type of CompoundAlkaloids
    FormulaC11H12N2O2Physical DescriptionCryst.
    Download     COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    Description: Tryptophan containing dipeptides are interesting ingredients for functional foods as a natural prevention for hypertension with reduced side effects due to its selective inhibition of the C-domain.Low thalamic Tryptophan uptake appears to be a strong, independent predictor of long survival in patients with previous glioma treatment.
    In vitro:
    Exp Eye Res. 2015 Jan;130:66-72.
    Differential tolerance of 'pseudo-pathogenic' tryptophan residues in calcium-binding EGF domains of short fibulin proteins.[Pubmed: 25481286]
    An Arg345Trp (R345W) mutation in the last canonical calcium-binding epidermal growth factor (cbEGF) domain of fibulin-3 (F3) causes the rare macular dystrophy, Malattia Leventinese (ML). In cell culture studies, this mutation leads to inefficient F3 secretion and higher intracellular steady state levels, likely due to F3 disulfide bonding and/or protein folding problems. However, how the R345W mutation actually causes ML is still largely unknown.
    METHODS AND RESULTS:
    Herein we tested whether the introduction of analogous, 'pseudo-pathogenic' Tryptophan mutations immediately after the bn cysteine (bn+1) in other cbEGF domains also caused protein folding/secretion challenges. We found that introduction of Tryptophan mutations into each of the four other F3 canonical cbEGF domains caused a significant reduction in protein secretion ranging from 2.7 to 56% of wild-type (WT) F3 levels. Surprisingly, an R185W mutation in the first canonical cbEGF domain of F3 yielded the highest amount of secretion among the F3 Tryptophan mutants, and its secretion defect could be rescued to near WT levels (95%) after growth temperature reduction. Interestingly, when similarly positioned Tryptophan mutations were introduced into any of the canonical cbEGF domains of the highly homologous protein, fibulin-5 (F5), there was no effect on secretion. In an attempt to make F3 tolerant of Tryptophan residues (like F5), we genetically engineered F3 to have a higher sequence homology with F5 by deleting three insert regions present in F3, but not F5. However, deletion of one or more of these regions did not have a beneficial effect on R345W F3 secretion.
    CONCLUSIONS:
    Overall, these results demonstrate that the introduction of Tryptophan residues at the bn+1 position does not universally disrupt cbEGF domain folding and secretion, but that their effect is context dependent, and in this case, uniquely disrupt the folding of canonical cbEGF domains of F3, but not F5.
    Tryptophan Description
    Source: The seeds of Glycine max
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 4.8967 mL 24.4834 mL 48.9668 mL 97.9336 mL 122.417 mL
    5 mM 0.9793 mL 4.8967 mL 9.7934 mL 19.5867 mL 24.4834 mL
    10 mM 0.4897 mL 2.4483 mL 4.8967 mL 9.7934 mL 12.2417 mL
    50 mM 0.0979 mL 0.4897 mL 0.9793 mL 1.9587 mL 2.4483 mL
    100 mM 0.049 mL 0.2448 mL 0.4897 mL 0.9793 mL 1.2242 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Structure Identification:
    Food Chem. 2015 Jan 1;166:596-602.
    Tryptophan-containing dipeptides are C-domain selective inhibitors of angiotensin converting enzyme.[Pubmed: 25053098]
    Somatic angiotensin-converting enzyme (ACE) contains two active sites, the C- and N-domain, from which the C-domain is supposed to play a major role in blood pressure regulation and is therefore a promising pharmacological target to reduce blood pressure without side-effects.
    METHODS AND RESULTS:
    We report for the first time that Tryptophan-containing dipeptides such as Ile-Trp or Val-Trp, which were recently found in food protein hydrolysates, are selective and competitive inhibitors for the C-domain with a selectivity factor of 40 and 70, respectively. Structure-activity studies showed that an N-terminal aliphatic amino acid and a Tryptophan moiety in the P2' position are favourable structures for C-domain inhibition in dipeptides. In contrast, the lactotripeptides Ile-Pro-Pro and Val-Pro-Pro, which were widely used as ingredients for hypotensive food, showed a slight selectivity for the N-domain.
    CONCLUSIONS:
    Hence, Tryptophan containing dipeptides are interesting ingredients for functional foods as a natural prevention for hypertension with reduced side effects due to its selective inhibition of the C-domain.
    J Nucl Med. 2014 Oct;55(10):1605-10.
    Clinical significance of tryptophan metabolism in the nontumoral hemisphere in patients with malignant glioma.[Pubmed: 25189339]

    METHODS AND RESULTS:
    Herein we tested whether the introduction of analogous, 'pseudo-pathogenic' Tryptophan mutations immediately after the bn cysteine (bn+1) in other cbEGF domains also caused protein folding/secretion challenges. We found that introduction of Tryptophan mutations into each of the four other F3 canonical cbEGF domains caused a significant reduction in protein secretion ranging from 2.7 to 56% of wild-type (WT) F3 levels. Surprisingly, an R185W mutation in the first canonical cbEGF domain of F3 yielded the highest amount of secretion among the F3 Tryptophan mutants, and its secretion defect could be rescued to near WT levels (95%) after growth temperature reduction. Interestingly, when similarly positioned Tryptophan mutations were introduced into any of the canonical cbEGF domains of the highly homologous protein, fibulin-5 (F5), there was no effect on secretion. In an attempt to make F3 tolerant of Tryptophan residues (like F5), we genetically engineered F3 to have a higher sequence homology with F5 by deleting three insert regions present in F3, but not F5. However, deletion of one or more of these regions did not have a beneficial effect on R345W F3 secretion.
    CONCLUSIONS:
    Overall, these results demonstrate that the introduction of Tryptophan residues at the bn+1 position does not universally disrupt cbEGF domain folding and secretion.