OF4949 III
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03314 |
| CAS | 107140-32-9 |
| Molecular Weight | 470.5 |
| Molecular Formula | C23H26N4O7 |
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Description
OF4949 III is an aminopeptidase B produced by Penicillum rugulosum OF4949.
Specification
| Synonyms | OF 4949III; OF 4949-III; OF4949III |
| IUPAC Name | (9S,12S,15S)-9-amino-12-(2-amino-2-oxoethyl)-4-methoxy-10,13-dioxo-2-oxa-11,14-diazatricyclo[15.2.2.13,7]docosa-1(19),3,5,7(22),17,20-hexaene-15-carboxylic acid |
| Canonical SMILES | COC1=C2C=C(CC(C(=O)NC(C(=O)NC(CC3=CC=C(O2)C=C3)C(=O)O)CC(=O)N)N)C=C1 |
| InChI | InChI=1S/C23H26N4O7/c1-33-18-7-4-13-8-15(24)21(29)26-16(11-20(25)28)22(30)27-17(23(31)32)9-12-2-5-14(6-3-12)34-19(18)10-13/h2-7,10,15-17H,8-9,11,24H2,1H3,(H2,25,28)(H,26,29)(H,27,30)(H,31,32)/t15-,16-,17-/m0/s1 |
| InChI Key | GDRXSYCFWCIGRB-ULQDDVLXSA-N |
Reference Reading
1. OF4949, new inhibitors of aminopeptidase B. II. Elucidation of structure
S Sano, K Ikai, K Katayama, K Takesako, T Nakamura, A Obayashi, Y Ezure, H Enomoto J Antibiot (Tokyo). 1986 Dec;39(12):1685-96. doi: 10.7164/antibiotics.39.1685.
The structures of OF4949-I, II, III and IV were identified by analysis of the products of their chemical degradation and by 1H NMR, 13C NMR, and mass spectrometry. These compounds were new cyclic peptides containing diphenyl ether as a chromophore. OF4949-I had two amino acids, beta-hydroxy-L-asparagine and 4-methylisodityrosine. The structural differences between I and II and between III and IV lay solely in the diphenyl ether moiety; the phenolic hydroxyl group in II and IV was methylated in I and III. OF4949-III and IV contained L-asparagine instead of the beta-hydroxy-L-asparagine moiety of I and II.
2. OF4949, new inhibitors of aminopeptidase B. III. Biosynthesis
S Sano, M Ueno, K Katayama, T Nakamura, A Obayashi J Antibiot (Tokyo). 1986 Dec;39(12):1697-703. doi: 10.7164/antibiotics.39.1697.
To elevate production of OF4949 by Penicillium rugulosum OF4949 and to elucidate the pathway of its biosynthesis, mutants were selected on the basis of their resistance to growth inhibition by phenylalanine analogs. A mutant resistant to m-fluorophenylalanine, strain No. M414, had 3-fold the production of the parent. In a study of the biosynthesis of OF4949-I and II, several 14C-labeled compounds were examined as possible precursors of OF4949. L-[14C]Tyrosine and L-[14C]asparagine were incorporated efficiently. Most of the radioactivity of L-[14C]tyrosine was found in the 4-methylisodityrosine (B2) or isodityrosine (B1) moieties, and that of L-[14C]asparagine was in the beta-hydroxyasparagine moiety.
3. Application of Negishi cross-coupling to the synthesis of the cyclic tripeptides OF4949-III and K-13
Luca Nolasco, Manuel Perez Gonzalez, Lorenzo Caggiano, Richard F W Jackson J Org Chem. 2009 Nov 6;74(21):8280-9. doi: 10.1021/jo9018792.
Syntheses of the cyclic tripeptides OF4949-III 1 and K-13 2 are reported, in which the key steps are intermolecular and intramolecular Negishi cross-coupling reactions, respectively. In addition, the synthesis of a protected isomer of K-13 25 is reported. The synthesis of K-13 features a tripeptidic organozinc reagent 11, one of the most highly functionalized such reagents to be described. An O-aryltyrosine derivative 15, prepared by S(N)Ar reaction between Boc-tyrosine and 2-fluorobenzaldehyde, followed by Dakin reaction, iodination, and methylation, is used as a common intermediate for all of the syntheses described. The routes to this class of cyclic tripeptide are among the shortest reported to date and demonstrate the high functional group tolerance of the carbon-zinc bond toward peptide derivatives.
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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 ╳
