Trestatin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02709 |
| CAS | 71892-68-7 |
| Molecular Weight | 1900.78 |
| Molecular Formula | C75H125N3O52 |
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Description
It is produced by the strain of Str. dimorphogenes NR-320-OM7HB. Trestatin C has a strong inhibitory effect on pancreatic α-amylase, and also inhibits the α-amylase of Bacillus subtilis and Aspergillus oryzae.
Specification
| Synonyms | Ro 09-0185 |
| IUPAC Name | (2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-5-[[(1S,4R,5R,6S)-4-[(2S,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-5-[[(4R,5R,6S)-4-[(2S,3R,4R,5S,6R)-5-[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]-3,4-dihydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(C(C(C=C3CO)NC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(C(C(C=C6CO)NC7C(OC(C(C7O)O)OC8C(OC(C(C8O)O)OC9C(OC(C(C9O)O)OC1C(OC(C(C1O)O)OC1C(C(C(C(O1)CO)O)O)O)CO)CO)CO)C)O)O)CO)C)O)O)CO)O)O)NC1C=C(C(C(C1O)O)O)CO |
| InChI | InChI=1S/C75H125N3O52/c1-16-31(76-22-4-19(7-79)34(88)42(96)35(22)89)39(93)51(105)67(114-16)125-62-26(11-83)118-70(55(109)46(62)100)123-60-20(8-80)5-23(36(90)44(60)98)77-32-17(2)115-68(52(106)40(32)94)126-63-27(12-84)119-71(56(110)47(63)101)124-61-21(9-81)6-24(37(91)45(61)99)78-33-18(3)116-69(53(107)41(33)95)127-64-28(13-85)120-72(57(111)48(64)102)128-65-29(14-86)121-73(58(112)49(65)103)129-66-30(15-87)122-75(59(113)50(66)104)130-74-54(108)43(97)38(92)25(10-82)117-74/h4-6,16-18,22-113H,7-15H2,1-3H3/t16-,17-,18-,22?,23?,24+,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35+,36+,37+,38-,39+,40+,41+,42+,43+,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-/m1/s1 |
| InChI Key | OBZZPMPQQQMTMK-FPAWZWHZSA-N |
Properties
| Appearance | Colorless Powder |
| Melting Point | 230-237°C |
| Density | 1.82 g/cm3 |
Reference Reading
1. Inhibition of selectin-mediated cell adhesion and prevention of acute inflammation by nonanticoagulant sulfated saccharides. Studies with carboxyl-reduced and sulfated heparin and with trestatin a sulfate
X Xie, A S Rivier, A Zakrzewicz, M Bernimoulin, X L Zeng, H P Wessel, M Schapira, O Spertini J Biol Chem. 2000 Nov 3;275(44):34818-25. doi: 10.1074/jbc.M001257200.
Selectins play a major role in the inflammatory reaction by initiating neutrophil attachment to activated vascular endothelium. Some heparin preparations can interact with L- and P-selectin; however, the determinants required for inhibiting selectin-mediated cell adhesion have not yet been characterized. We now report that carboxyl-reduced and sulfated heparin (prepared by chemical modifications of porcine intestinal mucosal heparin leading to the replacement of carboxylates by O-sulfate groups) and trestatin A sulfate (obtained by sulfation of trestatin A, a non-uronic pseudo-nonasaccharide extracted from Streptomyces dimorphogenes) exhibit strong anti-P-selectin and anti-L-selectin activity while lacking antithrombin-mediated anticoagulant activity. In vitro experiments revealed that both compounds inhibited P-selectin- and L-selectin-mediated cell adhesion under laminar flow conditions. Moreover, carboxyl-reduced and sulfated heparin and trestatin A sulfate were also active in vivo, as assessed by experiments showing 1) that microinfusion of trestatin A sulfate reduced by 96% leukocyte rolling along rat mesenteric postcapillary venules and 2) that both compounds inhibited (by 58-81%) neutrophil migration into thioglycollate-inflamed peritoneum of BALB/c mice. These results indicate that nonanticoagulant sulfated saccharides targeted at P-selectin and L-selectin may have therapeutic potential in inflammatory disorders.
2. Crystal structures of human pancreatic alpha-amylase in complex with carbohydrate and proteinaceous inhibitors
V Nahoum, G Roux, V Anton, P Rougé, A Puigserver, H Bischoff, B Henrissat, F Payan Biochem J. 2000 Feb 15;346 Pt 1(Pt 1):201-8.
Crystal structures of human pancreatic alpha-amylase (HPA) in complex with naturally occurring inhibitors have been solved. The tetrasaccharide acarbose and a pseudo-pentasaccharide of the trestatin family produced identical continuous electron densities corresponding to a pentasaccharide species, spanning the -3 to +2 subsites of the enzyme, presumably resulting from transglycosylation. Binding of the acarviosine core linked to a glucose residue at subsites -1 to +2 appears to be a critical part of the interaction process between alpha-amylases and trestatin-derived inhibitors. Two crystal forms, obtained at different values of pH, for the complex of HPA with the protein inhibitor from Phaseolus vulgaris (alpha-amylase inhibitor) have been solved. The flexible loop typical of the mammalian alpha-amylases was shown to exist in two different conformations, suggesting that loop closure is pH-sensitive. Structural information is provided for the important inhibitor residue, Arg-74, which has not been observed previously in structural analyses.
3. Acarbose May Function as a Competitive Exclusion Agent for the Producing Bacteria
Samuel Tanoeyadi, Takeshi Tsunoda, Takuya Ito, Benjamin Philmus, Taifo Mahmud ACS Chem Biol. 2023 Feb 17;18(2):367-376. doi: 10.1021/acschembio.2c00795. Epub 2023 Jan 17.
Acarbose is a well-known microbial specialized metabolite used clinically to treat type 2 diabetes. This natural pseudo-oligosaccharide (PsOS) shows potent inhibitory activity toward various glycosyl hydrolases, including α-glucosidases and α-amylases. While acarbose and other PsOSs are produced by many different bacteria, their ecological or biological role in microbial communities is still an open question. Here, we show that several PsOS-producing actinobacteria, i.e., Actinoplanes sp. SE50/110 (acarbose producer), Streptomyces glaucescens GLA.O (acarbose producer), and Streptomyces dimorphogenes ATCC 31484 (trestatin producer), can grow in the presence of acarbose, while the growth of the non-PsOS-producing organism Streptomyces coelicolor M1152 was suppressed when starch is the main source of energy. Further investigations using recombinant α-amylases from S. coelicolor M1152 and the PsOS-producing actinobacteria revealed that the S. coelicolor α-amylase was inhibited by acarbose, whereas those from the PsOS-producing bacteria were not inhibited by acarbose. Bioinformatic and protein modeling studies suggested that a point mutation in the α-amylases of the PsOS-producing actinobacteria is responsible for the resistance of those enzymes toward acarbose. Converting the acarbose-resistant α-amylase AcbE to its A304H variant diminished its acarbose-resistance property. Taken together, the results suggest that acarbose is used by the producing bacteria as a competitive exclusion agent to suppress the growth of other microorganisms in their natural environment, while the producing organisms equip themselves with α-amylase variants that are resistant to acarbose.
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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 ╳
