Tyropeptin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02735 |
| CAS | |
| Molecular Weight | 511.61 |
| Molecular Formula | C28H37N3O6 |
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Description
It is produced by the strain of Kitasatospora sp. MK993-dF2. The inhibitory activity of B against CHT-L and T-L of 20S proteasome was half that of A.
Specification
| Synonyms | n-butyryl-L-tyrosyl-L-leucyl-DL-tyrosynal |
| IUPAC Name | (2S)-2-[[(2S)-2-(butanoylamino)-3-(4-hydroxyphenyl)propanoyl]amino]-N-[1-(4-hydroxyphenyl)-3-oxopropan-2-yl]-4-methylpentanamide |
| Canonical SMILES | CCCC(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(CC(C)C)C(=O)NC(CC2=CC=C(C=C2)O)C=O |
| InChI | InChI=1S/C28H37N3O6/c1-4-5-26(35)30-25(16-20-8-12-23(34)13-9-20)28(37)31-24(14-18(2)3)27(36)29-21(17-32)15-19-6-10-22(33)11-7-19/h6-13,17-18,21,24-25,33-34H,4-5,14-16H2,1-3H3,(H,29,36)(H,30,35)(H,31,37)/t21?,24-,25-/m0/s1 |
| InChI Key | SYAOZPXWOOYNES-MHKYCTGGSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 91-94°C |
Reference Reading
1. Tyropeptins A and B, new proteasome inhibitors produced by Kitasatospora sp. MK993-dF2. I. Taxonomy, isolation, physico-chemical properties and biological activities
I Momose, R Sekizawa, H Hashizume, N Kinoshita, Y Homma, M Hamada, H Iinuma, T Takeuchi J Antibiot (Tokyo). 2001 Dec;54(12):997-1003. doi: 10.7164/antibiotics.54.997.
Tyropeptins A and B, new proteasome inhibitors, were isolated from the culture broth of Kitasatospora sp. MK993-dF2. They were purified using ethyl acetate extraction, silica gel column chromatography, Sephadex LH-20 column chromatography and HPLC. Tyropeptin A inhibited the chymotrypsin-like (ChT-L) and trypsin-like (T-L) activities of 20S proteasome with IC50 values of 0.1 microg/ml and 1.5 microg/ml respectively, but did not inhibit the peptidylglutamyl-peptide hydrolyzing (PGPH) activity of 20S proteasome at a concentration of 100 microg/ml. The inhibitory activities of tyropeptin A were about two times as strong as that of tyropeptin B. Taxonomy of the producing strain is also described.
2. Synthesis of boronic acid derivatives of tyropeptin: proteasome inhibitors
Takumi Watanabe, Isao Momose, Masatoshi Abe, Hikaru Abe, Ryuichi Sawa, Yoji Umezawa, Daishiro Ikeda, Yoshikazu Takahashi, Yuzuru Akamatsu Bioorg Med Chem Lett. 2009 Apr 15;19(8):2343-5. doi: 10.1016/j.bmcl.2009.02.117. Epub 2009 Mar 4.
Boronic acid derivatives of tyropeptin were synthesized with TP-110 as the lead compound. Due to the lability of the aminoboronic acid moiety, careful design of the deprotection and coupling sequence was required. Liquid-liquid partition chromatography was found to be a powerful tool for purification of compounds of this class. The obtained derivatives showed potent inhibitory activities against the human 20S proteasome in vitro.
3. Tyropeptins, proteasome inhibitors produced by Kitasatospora sp. MK993-dF2
Isao Momose, Takumi Watanabe J Antibiot (Tokyo). 2017 May;70(5):542-550. doi: 10.1038/ja.2017.9. Epub 2017 Feb 15.
Tyropeptins are new proteasome inhibitors isolated from the culture broth of Kitasatospora sp. MK993-dF2. Tyropeptins permeate cell membranes, inhibit intracellular proteasomes and reduce the degradation of ubiquitinated proteins in mammalian cells. We performed structure-based drug design and structure-activity relationship studies on tyropeptin derivatives to obtain valuable information of derivatives. Among the synthesized tyropeptin derivatives, some boronic acid derivatives exhibited potent antitumor effects against human multiple myeloma. In this review, we summarize the discovery of tyropeptins and the development of tyropeptin derivatives.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
