PM-94128
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| Category | Antibiotics |
| Catalog number | BBF-03345 |
| CAS | 182292-49-5 |
| Molecular Weight | 422.5 |
| Molecular Formula | C22H34N2O6 |
Online Inquiry
Description
PM-94128
Specification
| Synonyms | PM 94128; PM94128 |
| IUPAC Name | (2S,3S,4S)-4-amino-2,3-dihydroxy-N-[(1S)-1-[(3S)-8-hydroxy-1-oxo-3,4-dihydroisochromen-3-yl]-3-methylbutyl]-6-methylheptanamide |
| Canonical SMILES | CC(C)CC(C1CC2=C(C(=CC=C2)O)C(=O)O1)NC(=O)C(C(C(CC(C)C)N)O)O |
| InChI | InChI=1S/C22H34N2O6/c1-11(2)8-14(23)19(26)20(27)21(28)24-15(9-12(3)4)17-10-13-6-5-7-16(25)18(13)22(29)30-17/h5-7,11-12,14-15,17,19-20,25-27H,8-10,23H2,1-4H3,(H,24,28)/t14-,15-,17-,19-,20-/m0/s1 |
| InChI Key | ZGMSHKBULLTJHQ-UHBFJLORSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 172-173°C |
Reference Reading
1. Asymmetric total synthesis and stereochemical elucidation of the antitumor agent PM-94128
Samir K Patel, Karine Murat, Sandrine Py, Yannick Vallée Org Lett. 2003 Oct 30;5(22):4081-4. doi: 10.1021/ol035470n.
[reaction: see text]. PM-94128, a novel depsipeptide antitumor agent, has been synthesized for the first time through a highly stereocontrolled route. The key steps for the synthesis of the dihydroxyamino acid moiety involve a diastereoselective addition of tert-butyl lithiopropiolate to a chiral nitrone and a 2,3-dihydro[1,2]oxazin-6-one dihydroxylation. The synthesis serves to define the relative as well as the absolute configuration of the natural product (bearing five stereogenic centers).
2. Concise synthesis of PM-94128 and Y-05460M-A
Masaru Enomoto, Shigefumi Kuwahara J Org Chem. 2009 Oct 2;74(19):7566-9. doi: 10.1021/jo9014968.
The enantioselective total synthesis of PM-94128, a potent cytotoxin of microbial origin, was accomplished by a concise nine-step sequence of reactions in 14% overall yield from N-Boc-l-leucine. The synthesis of Y-05460M-A, a one-carbon lower homologue of PM-94128, was also achieved from N-Boc-l-valine by the same approach, which enabled its stereochemical determination.
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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 ╳
