Phepropeptin A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02399 |
| CAS | |
| Molecular Weight | 682.89 |
| Molecular Formula | C37H58N6O6 |
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Description
It is produced by the strain of Streptomyces sp. MK600-cF7. It can inhibit the activity of Proteasome with IC50 of 21.0 μg/mL.
Specification
| IUPAC Name | (3R,6S,9S,12R,15S,18S)-3-benzyl-6,12,15-tris(2-methylpropyl)-9-propan-2-yl-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosane-2,5,8,11,14,17-hexone |
| Canonical SMILES | CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)N1)CC3=CC=CC=C3)CC(C)C)C(C)C)CC(C)C |
| InChI | InChI=1S/C37H58N6O6/c1-21(2)17-26-32(44)38-28(19-23(5)6)34(46)42-31(24(7)8)36(48)40-27(18-22(3)4)33(45)41-29(20-25-13-10-9-11-14-25)37(49)43-16-12-15-30(43)35(47)39-26/h9-11,13-14,21-24,26-31H,12,15-20H2,1-8H3,(H,38,44)(H,39,47)(H,40,48)(H,41,45)(H,42,46)/t26-,27-,28+,29+,30-,31-/m0/s1 |
| InChI Key | QVOWLQGIVUTHGK-ZAFXZDQFSA-N |
Properties
| Appearance | White Powder |
| Melting Point | 115-117°C |
| Solubility | Soluble in Methanol |
Reference Reading
1. Isolation and structural determination of phepropeptins A, B, C, and D, new proteasome inhibitors, produced by Streptomyces sp
R Sekizawa, I Momose, N Kinoshita, H Naganawa, M Hamada, Y Muraoka, H Iinuma, T Takeuchi J Antibiot (Tokyo). 2001 Nov;54(11):874-81. doi: 10.7164/antibiotics.54.874.
We have isolated four related compounds named phepropeptins A, B, C, and D, as inhibitors of proteasome proposed to regulate many cellular functions. From an NMR analysis, the phepropeptins appeared as cyclic hexapeptides, differing in the two residues of the constituent amino acids from one another, with four conserved amino acid moieties. Based on an amino acid analysis, we synthesized two possible cyclic peptides to phepropeptin B that differ in the configurations. A comparison of the properties between the natural and synthesized compounds revealed that the structure of phepropeptin B was cyclo(-L-Leu-D-Phe-L-Pro-L-Phe-D-Leu-L-Val-). The phepropeptins showed inhibition to the proteasomal chymotrypsin-like activity but not to alpha-chymotrypsin.
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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 ╳
