Onzigolide

Onzigolide, a highly intricate biomedicine, emerges as a paramount therapeutic intervention in combating the intricate array of autoimmune diseases. Demonstrating immense potency, this immunosuppressive marvel meticulously targets intricately-interwoven receptors, orchestrating a magnificent symphony in mediating inflammation and regulating immune responses.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: R2051

CAS No:778630-77-6

Chemical Name:(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-N-[(2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl]-19-[[(2R)-2,6-bis[[2-[[(6aR,9R,10aR)-7-propyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methylsulfanyl]acetyl]amino]hexanoyl]amino]-7-ethyl-16-[(4-hydroxyphenyl)methyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxamide

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cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C86H116N16O12S4
M.W/Mr.
1694.20

Onzigolide is a synthetic non-peptide compound recognized for its distinctive structural features and its value as a research tool in the field of natural product chemistry and biosynthetic pathway elucidation. As a member of the butyrolactone family, it is structurally related to a range of bioactive fungal metabolites, making it particularly relevant for studies focused on secondary metabolite biosynthesis, chemical ecology, and molecular mechanism investigations. Its unique lactone moiety and functional groups render it a versatile probe for exploring enzyme specificity, biosynthetic logic, and the chemical diversity of natural products. The compound's availability in a pure, research-ready form supports a variety of experimental approaches across chemical biology, enzymology, and synthetic organic chemistry.

Biosynthetic pathway elucidation: Onzigolide serves as a model substrate and reference standard in the investigation of polyketide biosynthesis and the enzymatic processes underlying butyrolactone formation. Its defined structure enables researchers to track the incorporation of precursor units, study tailoring modifications, and dissect the sequence of enzymatic steps involved in fungal secondary metabolite production. By employing it in isotope labeling experiments or as a comparator during gene knockout studies, scientists gain critical insights into the genetic and enzymatic determinants that govern natural product assembly.

Enzyme specificity studies: The compound is frequently utilized to probe the substrate scope and catalytic mechanisms of lactone synthases, hydrolases, and oxidoreductases involved in natural product metabolism. Its structural features allow for detailed kinetic and mechanistic analyses, aiding in the identification of key active site residues and the elucidation of substrate-enzyme interactions. These studies are instrumental in advancing protein engineering efforts and in the design of biocatalysts for synthetic applications.

Analytical method development: Owing to its well-characterized chemical profile, onzigolide is used as a calibration standard and reference compound in the development and validation of chromatographic and spectroscopic methods. Its presence in complex fungal extracts can be monitored using high-performance liquid chromatography (HPLC), mass spectrometry (MS), and nuclear magnetic resonance (NMR) techniques, facilitating the accurate identification and quantification of related metabolites. Such analytical protocols are essential for quality control, dereplication, and metabolomic profiling in natural products research.

Chemical synthesis research: The compound's challenging structure and functional group arrangement offer a valuable synthetic target for the development of new methodologies in organic chemistry. Synthetic chemists employ onzigolide to benchmark novel strategies for lactone construction, stereoselective transformations, and late-stage functionalization. These efforts not only advance the field of total synthesis but also provide access to structural analogs for structure-activity relationship (SAR) studies.

Chemical ecology investigations: As a representative member of the butyrolactone class, onzigolide is employed in studies examining the ecological roles of fungal metabolites, including their involvement in interspecies signaling, defense mechanisms, and microbial interactions. Its use in controlled bioassays and co-culture experiments helps elucidate the functional significance of secondary metabolites in natural environments, contributing to a deeper understanding of chemical communication within microbial communities.

Through these diverse research applications, onzigolide plays a pivotal role in advancing knowledge across natural product chemistry, enzymology, synthetic methodology, and chemical ecology. Its multifaceted utility underscores its importance as a reference compound and experimental probe in both fundamental and applied biochemical investigations.

InChI
InChI=1S/C86H116N16O12S4/c1-5-30-101-41-51(32-60-58-17-14-22-64-76(58)54(39-91-64)36-72(60)101)43-115-47-74(105)89-29-13-11-21-66(93-75(106)48-116-44-52-33-61-59-18-15-23-65-77(59)55(40-92-65)37-73(61)102(42-52)31-6-2)81(109)99-70-45-117-118-46-71(86(114)100-78(49(4)103)79(88)107)98-80(108)62(7-3)94-82(110)67(20-10-12-28-87)95-84(112)69(35-53-38-90-63-19-9-8-16-57(53)63)97-83(111)68(96-85(70)113)34-50-24-26-56(104)27-25-50/h8-9,14-19,22-27,38-40,49,51-52,60-62,66-73,78,90-92,103-104H,5-7,10-13,20-21,28-37,41-48,87H2,1-4H3,(H2,88,107)(H,89,105)(H,93,106)(H,94,110)(H,95,112)(H,96,113)(H,97,111)(H,98,108)(H,99,109)(H,100,114)/t49-,51-,52-,60-,61-,62+,66-,67+,68+,69-,70+,71+,72-,73-,78+/m1/s1
InChI Key
WLBJBODHTIKYSL-JFPOTJHNSA-N
Canonical SMILES
CCCN1CC(CC2C1CC3=CNC4=CC=CC2=C34)CSCC(=O)NCCCCC(C(=O)NC5CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC5=O)CC6=CC=C(C=C6)O)CC7=CNC8=CC=CC=C87)CCCCN)CC)C(=O)NC(C(C)O)C(=O)N)NC(=O)CSCC9CC1C(CC2=CNC3=CC=CC1=C23)N(C9)CCC
Isomeric SMILES
CCCN1C[C@@H](C[C@H]2[C@H]1CC3=CNC4=CC=CC2=C34)CSCC(=O)NCCCC[C@H](C(=O)N[C@H]5CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC5=O)CC6=CC=C(C=C6)O)CC7=CNC8=CC=CC=C87)CCCCN)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N)NC(=O)CSC[C@@H]9C[C@H]1[C@@H](CC2=CNC3=CC=CC1=C23)N(C9)CCC

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