Phenylalanyl-prolyl Diketopiperazine
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| Category | Mycotoxins |
| Catalog number | BBF-04406 |
| CAS | 26488-24-4 |
| Molecular Weight | 244.29 |
| Molecular Formula | C14H16N2O2 |
| Purity | 98.0% |
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Description
Cyclo(D-Phe-L-Pro) is a cyclodipeptide phytotoxin produced by Alternaria alternata and streptomyces rochei.
Specification
| Synonyms | L-Phe-L-Pro lactam; (3R,8aS)-Cyclo(phenylalanylprolyl); phenylalanyl-prolyl diketopiperazine; Cyclo(L-prolyl-D-phenylalanyl) |
| Storage | Store at -20°C |
| IUPAC Name | (3R,8aS)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione |
| Canonical SMILES | C1CC2C(=O)NC(C(=O)N2C1)CC3=CC=CC=C3 |
| InChI | InChI=1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12+/m1/s1 |
| InChI Key | QZBUWPVZSXDWSB-NEPJUHHUSA-N |
Properties
| Appearance | Oily Matter |
| Boiling Point | 509.5°C at 760 mmHg |
| Melting Point | 150-153°C |
| Density | 1.26 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1. Absence of pantothenic acid in gramicidin S synthetase 2 obtained from some mutants of Bacillus brevis
K Hori, M Kanda, T Kurotsu, S Miura, Y Yamada, Y Saito J Biochem. 1981 Aug;90(2):439-47. doi: 10.1093/oxfordjournals.jbchem.a133491.
The pantothenic acid content of gramicidin S synthetase 2(GS 2) was estimated microbiologically with enzymes obtained from the wild strain and gramicidin S-lacking mutant strains of Bacillus brevis. Four mutant enzymes from BI-4, C-3, E-1, and E-2 lacked pantothenic acid. Other mutant enzymes from BII-3, BI-3, BI-9, and BI-2 contained the same amount of pantothenic acid as the wild-type enzyme. Pantothenic acid-lacking GS 2 belonged to group V of mutant enzymes, which could activate all amino acids related to gramicidin S; their complementary enzyme, gramicidin S synthetase 1(GS 1), lacked racemizing activity. To ascertain whether 4'-phosphopantetheine is involved in the formation of D-phenylalanyl-L-prolyl diketopiperazine (DKP) and gramicidin S, combinations were tested of intact GS 1 from the wild strain with various mutant GS 2 either containing or lacking pantothenic acid. Only the combinations of wild-type GS 1 with mutant GS 2 containing pantothenic acid could synthesize DKP. Combinations with pantothenic acid-lacking GS 2 also failed to elongate peptide chains. Pantothenic acid-lacking GS 2 could bind the four amino acids which constitute gramicidin S as acyladenylates and thioesters, but the binding abilities were lower than those of the wild-type enzyme and other mutant enzymes containing the pantothenic group.
2. In Vitro Reconstruction of Nonribosomal Peptide Biosynthesis Directly from DNA Using Cell-Free Protein Synthesis
Anthony W Goering, Jian Li, Ryan A McClure, Regan J Thomson, Michael C Jewett, Neil L Kelleher ACS Synth Biol. 2017 Jan 20;6(1):39-44. doi: 10.1021/acssynbio.6b00160. Epub 2016 Aug 9.
Genome sequencing has revealed that a far greater number of natural product biosynthetic pathways exist than there are known natural products. To access these molecules directly and deterministically, a new generation of heterologous expression methods is needed. Cell-free protein synthesis has not previously been used to study nonribosomal peptide biosynthesis, and provides a tunable platform with advantages over conventional methods for protein expression. Here, we demonstrate the use of cell-free protein synthesis to biosynthesize a cyclic dipeptide with correct absolute stereochemistry. From a single-pot reaction, we measured the expression of two nonribosomal peptide synthetases larger than 100 kDa, and detected high-level production of a diketopiperazine. Using quantitative LC-MS and synthetically prepared standard, we observed production of this metabolite at levels higher than previously reported from cell-based recombinant expression, approximately 12 mg/L. Overall, this work represents a first step to apply cell-free protein synthesis to discover and characterize new natural products.
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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 ╳
