Tyropeptin A-4

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 598099

CAS#: 688737-89-5

Description: Tyropeptin A-4 is a proteasome inhibitor.


Chemical Structure

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Tyropeptin A-4
CAS# 688737-89-5

Theoretical Analysis

MedKoo Cat#: 598099
Name: Tyropeptin A-4
CAS#: 688737-89-5
Chemical Formula: C31H41N3O6
Exact Mass: 551.2995
Molecular Weight: 551.68
Elemental Analysis: C, 67.49; H, 7.49; N, 7.62; O, 17.40

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Tyropeptin A-4; Tyropeptin A 4; Tyropeptin A4; TP-101; TP 101; TP101;

IUPAC/Chemical Name: (2S)-2-((2S)-2-(2-cyclohexylacetamido)-3-(4-hydroxyphenyl)-N-(1-(4-hydroxyphenyl)-3-oxopropan-2-yl)propanamido)-3-methylbutanamide

InChi Key: OHEAMPJRQIBBHO-TXJYOHDVSA-N

InChi Code: InChI=1S/C31H41N3O6/c1-20(2)29(30(32)39)34(24(19-35)16-22-8-12-25(36)13-9-22)31(40)27(17-23-10-14-26(37)15-11-23)33-28(38)18-21-6-4-3-5-7-21/h8-15,19-21,24,27,29,36-37H,3-7,16-18H2,1-2H3,(H2,32,39)(H,33,38)/t24?,27-,29-/m0/s1

SMILES Code: CC(C)[C@@H](C(N)=O)N(C([C@H](CC1=CC=C(O)C=C1)NC(CC2CCCCC2)=O)=O)C(C=O)CC3=CC=C(O)C=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 551.68 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Momose I, Abe H, Watanabe T, Ohba S, Yamazaki K, Dan S, Yamori T, Masuda T, Nomoto A. Antitumor effects of tyropeptin-boronic acid derivatives: New proteasome inhibitors. Cancer Sci. 2014 Dec;105(12):1609-15. doi: 10.1111/cas.12542. Epub 2014 Oct 21. PubMed PMID: 25251038; PubMed Central PMCID: PMC4317970.

2: Watanabe T, Abe H, Momose I, Takahashi Y, Ikeda D, Akamatsu Y. Structure-activity relationship of boronic acid derivatives of tyropeptin: proteasome inhibitors. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5839-42. doi: 10.1016/j.bmcl.2010.07.122. Epub 2010 Aug 1. PubMed PMID: 20727746.

3: Steverding D, Pemberton AJ, Royle H, Spackman RW, Rivett AJ. Evaluation of the anti-trypanosomal activity of tyropeptin A. Planta Med. 2006 Jun;72(8):761-3. Epub 2006 May 29. PubMed PMID: 16732530.

4: Momose I, Umezawa Y, Hirosawa S, Iinuma H, Ikeda D. Structure-based design of derivatives of tyropeptin A as the potent and selective inhibitors of mammalian 20S proteasome. Bioorg Med Chem Lett. 2005 Apr 1;15(7):1867-71. PubMed PMID: 15780623.

5: Momose I, Sekizawa R, Iinuma H, Takeuchi T. Inhibition of proteasome activity by tyropeptin A in PC12 cells. Biosci Biotechnol Biochem. 2002 Oct;66(10):2256-8. PubMed PMID: 12450145.

6: Momose I, Umezawa Y, Hirosawa S, Iijima M, Iinuma H, Ikeda D. Synthesis and activity of tyropeptin A derivatives as potent and selective inhibitors of mammalian 20S proteasome. Biosci Biotechnol Biochem. 2005 Sep;69(9):1733-42. PubMed PMID: 16195592.

7: Watanabe T, Momose I, Abe M, Abe H, Sawa R, Umezawa Y, Ikeda D, Takahashi Y, Akamatsu Y. Synthesis of boronic acid derivatives of tyropeptin: proteasome inhibitors. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2343-5. doi: 10.1016/j.bmcl.2009.02.117. Epub 2009 Mar 4. PubMed PMID: 19307118.

8: Liu J, Zhang H, Xiao Z, Wang F, Wang X, Wang Y. Combined 3D-QSAR, molecular docking and molecular dynamics study on derivatives of peptide epoxyketone and tyropeptin-boronic acid as inhibitors against the β5 subunit of human 20S proteasome. Int J Mol Sci. 2011;12(3):1807-35. doi: 10.3390/ijms12031807. Epub 2011 Mar 9. PubMed PMID: 21673924; PubMed Central PMCID: PMC3111635.

9: Momose I, Sekizawa R, Hashizume H, Kinoshita N, Homma Y, Hamada M, Iinuma H, Takeuchi T. Tyropeptins A and B, new proteasome inhibitors produced by Kitasatospora sp. MK993-dF2. I. Taxonomy, isolation, physico-chemical properties and biological activities. J Antibiot (Tokyo). 2001 Dec;54(12):997-1003. PubMed PMID: 11858671.

10: Momose I, Iijima M, Kawada M, Ikeda D. A new proteasome inhibitor, TP-110, induces apoptosis in human prostate cancer PC-3 cells. Biosci Biotechnol Biochem. 2007 Apr;71(4):1036-43. Epub 2007 Apr 7. PubMed PMID: 17420589.

11: Momose I, Watanabe T. Tyropeptins, proteasome inhibitors produced by Kitasatospora sp. MK993-dF2. J Antibiot (Tokyo). 2017 May;70(5):542-550. doi: 10.1038/ja.2017.9. Epub 2017 Feb 15. Review. PubMed PMID: 28196975.