Shishijimicin A

Shishijimicin A is an enediyne antibiotic isolated from Didemnum proliferum.[1]

Shishijimicin A

Names
IUPAC name Methyl {(1R,4Z,8S,13Z)-8-({6-deoxy-2-O-[2,4-dideoxy-4-(isopropylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-4-C-[(6-hydroxy-9H-β-carbolin-1-yl)carbonyl]-4-S-methyl-4-thio-β-D-galactopyranosyl}oxy)-1-hydroxy-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl}carbamate
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	8388877
PubChem CID	10213385
InChI InChI=1S/C46H52N4O12S4/c1-24(2)48-31-23-59-35(21-34(31)57-4)62-40-42(54)46(63-6,41(53)39-37-27(15-18-47-39)28-20-26(51)13-14-30(28)49-37)25(3)60-43(40)61-33-12-10-8-9-11-17-45(56)22-32(52)38(50-44(55)58-5)36(33)29(45)16-19-65-66-64-7/h8-9,13-16,18,20,24-25,31,33-35,40,42-43,48-49,51,54,56H,19,21-23H2,1-7H3,(H,50,55)/b9-8-,29-16-/t25-,31+,33+,34+,35+,40-,42-,43+,45+,46-/m1/s1 Key: FVNYJZKDBPDHIP-UXLTXATLSA-N
SMILES CC1C(C(C(C(O1)OC2C#CC=CC#CC3(CC(=O)C(=C2C3=CCSSSC)NC(=O)OC)O)OC4CC(C(CO4)NC(C)C)OC)O)(C(=O)C5=NC=CC6=C5NC7=C6C=C(C=C7)O)SC
Properties
Chemical formula	C46H52N4O12S4
Molar mass	981.18 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

• Calicheamicin
• Esperamicin
• Kedarcidin
• Lidamycin

References

1. Nicolaou, K. C; Kiappes, J. L; Tian, W; Gondi, V. B; Becker, J (2011). "Synthesis of the Carboline Disaccharide Domain of Shishijimicin A". Organic Letters. 13 (15): 3924–7. doi:10.1021/ol201444t. PMC 3146563. PMID 21711032.