Padanamide A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03763 |
| CAS | 1314881-80-5 |
| Molecular Weight | 661.74 |
| Molecular Formula | C31H47N7O9 |
| Purity | ≥95% |
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Description
Padanamide A is a metabolite produced by marine Streptomyces species. It inhibits cysteine and methionine biosynthesis.
Specification
| Synonyms | Actinoramide A; CHEMBL3633597; CCG-208791 |
| Storage | Store at -20°C |
| IUPAC Name | (3S)-N-[(2S,3S,4S)-5-[[(3S)-1-carbamoyl-2-oxopyrrolidin-3-yl]amino]-3-hydroxy-4-methyl-5-oxo-1-phenylpentan-2-yl]-2-[(2R,3R)-3-hydroxy-2-[(2-methoxyacetyl)amino]-4-methylpentanoyl]diazinane-3-carboxamide |
| Canonical SMILES | CC(C)C(C(C(=O)N1C(CCCN1)C(=O)NC(CC2=CC=CC=C2)C(C(C)C(=O)NC3CCN(C3=O)C(=O)N)O)NC(=O)COC)O |
| InChI | InChI=1S/C31H47N7O9/c1-17(2)25(40)24(36-23(39)16-47-4)30(45)38-22(11-8-13-33-38)28(43)35-21(15-19-9-6-5-7-10-19)26(41)18(3)27(42)34-20-12-14-37(29(20)44)31(32)46/h5-7,9-10,17-18,20-22,24-26,33,40-41H,8,11-16H2,1-4H3,(H2,32,46)(H,34,42)(H,35,43)(H,36,39)/t18-,20-,21-,22-,24+,25+,26-/m0/s1 |
| InChI Key | IAYPOIKGUHHBAU-DYTCPEOESA-N |
Properties
| Appearance | Solid Powder |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Padanamides A and B, highly modified linear tetrapeptides produced in culture by a Streptomyces sp. isolated from a marine sediment
Chad L Myers, Jeff S Piotrowski, Teatulohi Matainaho, Raamesh Deshpande, Doralyn S Dalisay, David E Williams, Charles Boone, Kerry Andrusiak, Raymond J Andersen, Brian O Patrick, Minoru Yoshida Org Lett . 2011 Aug 5;13(15):3936-9. doi: 10.1021/ol2014494.
Two highly modified linear tetrapeptides, padanamides A (1) and B (2), are produced by laboratory cultures of a Streptomyces sp. obtained from a marine sediment. Padanamide B is cytotoxic to Jurkat cells, and a chemical genomics analysis using Saccharomyces cerevisiae deletion mutants suggested that padanamide A inhibits cysteine and methionine biosynthesis or that these amino acids are involved in the yeast's response to the peptide.
2. Total synthesis of padanamides A and B
Ligong Chen, Yuqing Liu, Bo Chen, Anita R Maguire, Zhuo Wang, Shoubin Tang, Tao Ye, Hui Zhang, Bohua Long, Junyang Liu, Shiwei Qu, Zhengshuang Xu Chem Commun (Camb) . 2013 Apr 14;49(29):2977-9. doi: 10.1039/c3cc00178d.
The first total syntheses of padanamides A and B have been achieved, unambiguously confirming their structures.
3. N-carbamoylation of 2,4-diaminobutyrate reroutes the outcome in padanamide biosynthesis
Raymond J Andersen, Katherine S Ryan, Yi-Ling Du, Doralyn S Dalisay Chem Biol . 2013 Aug 22;20(8):1002-11. doi: 10.1016/j.chembiol.2013.06.013.
Padanamides are linear tetrapeptides notable for the absence of proteinogenic amino acids in their structures. In particular, two unusual heterocycles, (S)-3-amino-2-oxopyrrolidine-1-carboxamide (S-Aopc) and (S)-3-aminopiperidine-2,6-dione (S-Apd), are found at the C-termini of padanamides A and B, respectively. Here we identify the padanamide biosynthetic gene cluster and carry out systematic gene inactivation studies. Our results show that padanamides are synthesized by highly dissociated hybrid nonribosomal peptide synthetase/polyketide synthase machinery. We further demonstrate that carbamoyltransferase gene padQ is critical to the formation of padanamide A but dispensable for biosynthesis of padanamide B. Biochemical investigations show that PadQ carbamoylates the rare biosynthetic precursor l-2,4-diaminobutyrate, generating l-2-amino-4-ureidobutyrate, the presumed precursor to the C-terminal residue of padanamide A. By contrast, the C-terminal residue of padanamide B may derive from glutamine. An unusual thioesterase-catalyzed cyclization is proposed to generate the S-Aopc/S-Apd heterocycles.
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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 ╳
