Talopeptin

Talopeptin

Names
IUPAC name (2S)-2-[[(2S)-2-[[hydroxy-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid
Other names N-[N-[[(6-deoxy-α-L-talopyranosyl)oxy]hydroxyphosphinyl]-L-leucyl]-L-tryptophan
Identifiers
CAS Number	84235-60-9
ChemSpider	118729
Jmol interactive 3D	Image
PubChem	134712
InChI InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18+,19+,20+,23-/m0/s1 Key: ZPHBZEQOLSRPAK-XVOJFHBISA-N InChI=1/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18+,19+,20+,23-/m0/s1 Key: ZPHBZEQOLSRPAK-XVOJFHBIBA
SMILES O=C(O)[C@@H](NC([C@H](CC(C)C)NP(O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@H]1O)(O)=O)=O)CC2=CNC3=C2C=CC=C3
Properties
Chemical formula	C23H34N3O10P
Molar mass	543.51 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Talopeptin is a chemical compound derived from cultures of Streptomyces. It is a known reversible inhibitor of thermolysin^[1] and is expected to inhibit other metalloproteinases.^[2][3] Chemically, talopeptin differs from its closely related peptidase inhibitorphosphoramidon by a single stereocenter.

References

1. Kitagishi, Keiko; Hiromi, Keitaro (1984). "Inhibitory spectrum of talopeptin (MKI), a specific inhibitor of thermolysin". Agricultural and Biological Chemistry 48 (5): 1287–91. doi:10.1271/bbb1961.48.1287.
2. Fukuhara, Kenichi; Murao, Sawao; Nozawa, Tsunenori; Hatano, Masahiro (1982). "Structural elucidation of talopeptin (MK-I), a novel metallo proteinase inhibitor produced by Streptomyces mozunensis MK-23". Tetrahedron Letters 23 (22): 2319–22. doi:10.1016/S0040-4039(00)87331-1.
3. Kitagishi, Keiko; Hiromi, Keitaro; Oda, Kohei; Murao, Sawao (1983). "Equilibrium study on the binding between thermolysin and Streptomyces metalloprotease inhibitor, talopeptin (MKI)". Journal of Biochemistry 93 (1): 47–53. PMID 6341369.

External links

• The MEROPS online database for peptidases and their inhibitors: Talopeptin