Fmoc-DL-Phe(3-NH2)-OH
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Fmoc-DL-Phe(3-NH2)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008229
CAS number
223581-75-7
Molecular Formula
C24H22N2O4
Molecular Weight
402.4
IUPAC Name
3-(3-aminophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
Synonyms
(2S)-3-(3-aminophenyl)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acid
Density
1.3±0.1 g/cm3
Boiling Point
674.9±55.0 °C at 760 mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C24H22N2O4/c25-16-7-5-6-15(12-16)13-22(23(27)28)26-24(29)30-14-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-12,21-22H,13-14,25H2,(H,26,29)(H,27,28)
InChI Key
ZNJZSLBSDBNOSV-UHFFFAOYSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC(=CC=C4)N)C(=O)O
1. Chemical substituent effect on pyridine permeability and mechanistic insight from computational molecular descriptors
I-Jen Chen, Rajneesh Taneja, Daxu Yin, Paul R Seo, David Young, Alexander D MacKerell Jr, James E Polli Mol Pharm. 2006 Nov-Dec;3(6):745-55. doi: 10.1021/mp050096+.
The objective was (1) to evaluate the chemical substituent effect on Caco-2 permeability, using a congeneric series of pyridines, and (2) compare molecular descriptors from a computational chemistry approach against molecular descriptors from the Hansch approach for their abilities to explain the chemical substituent effect on pyridine permeability. The passive permeability of parent pyridine and 14 monosubstituted pyridines were measured across Caco-2 monolayers. Computational chemistry analysis was used to obtain the following molecular descriptions: solvation free energies, solvent accessible surface area, polar surface area, and cavitation energy. Results indicate that the parent pyridine was highly permeable and that chemical substitution was able to reduce pyridine permeability almost 20-fold. The substituent effect on permeability provided the following rank order: 3-COO- < 4-NH2 < 3-CONH2 < 3-Cl < 3-CHO < 3-OH < 3-CH2OH < 3-C6H5 < 3-NH2 < 3-CH2C6H5 < 3-C2H5 < 3-H < 3-CH3 < 3-F < 4-C6H5. This substituent effect was better explained via molecule descriptors from the computational chemistry approach than explained by classic descriptors from Hansch. Computational descriptors indicate that aqueous desolvation, but not membrane partitioning per se, dictated substituent effect on permeability.
2. Broadband Microwave Spectroscopy of Prototypical Amino Alcohols and Polyamines: Competition between H-Bonded Cycles and Chains
Di Zhang, Sebastian Bocklitz, Timothy S Zwier J Phys Chem A. 2016 Jan 14;120(1):55-67. doi: 10.1021/acs.jpca.5b10650. Epub 2015 Dec 29.
The rotational spectra of the amino alcohols d-allo-threoninol, 2-amino-1,3-propanediol, and 1,3-diamino-2-propanol and the triamine analog, propane-1,2,3-triamine, have been investigated under jet-cooled conditions over the 7.5-18.5 GHz frequency range using chirped-pulsed Fourier transform microwave spectroscopy. Microwave transitions due to three conformers of d-allothreoninol, four conformers of 2-amino-1,3-propanediol, four conformers of 1,3-diamino-2-propanol, and four conformers of propane-1,2,3-triamine have been identified and assigned, aided by comparison of the fitted experimental rotational constants with the predictions for candidate structures based on an exhaustive conformational search using force field, ab initio and DFT methods. Distinctions between conformers with similar rotational constants were made on the basis of the observed nuclear quadrupole splittings and relative line strengths, which reflect the direction of the permanent dipole moment of the conformers. With three adjacent H-bonding substituents along the alkyl chain involving a combination of OH and NH2 groups, hydrogen-bonded cycles (3 H-bonds) and chains (2 H-bonds) remain close in energy, no matter what the OH/NH2 composition. Two families of H-bonded chains are possible, with H-bonding substituents forming curved chain or extended chain structures. Percent populations of the observed conformers were extracted from the relative intensities of their microwave spectra, which compare favorably with relative energies calculated at the B2PLYP-D3BJ/aug-cc-pVTZ level of theory. In glycerol (3 OH), d-allothreoninol (2 OH, 1 NH2), 2-amino-1,3-propanediol (2 OH, 1 NH2), and 1,3-diamino-2-propanol (1 OH, 2 NH2), H-bonded cycles are most highly populated, followed by curved chains (3 OH or 2 OH/1 NH2) or extended chains (1 OH/2 NH2). In propane-1,2,3-triamine (3 NH2), H-bonded cycles are pushed higher in energy than both curved and extended chains, which carry all the observed population. The NH2 group serves as a better H-bond acceptor than donor, as is evidenced by optimized structures in which H-bond lengths fall into the following order: r(OH···N) ≈ r(OH···O) < r(NH···N) ≈ r(NH···O).
3. Structure-activity relationships for antibacterial to antifungal conversion of kanamycin to amphiphilic analogues
Marina Fosso, et al. J Org Chem. 2015 May 1;80(9):4398-411. doi: 10.1021/acs.joc.5b00248. Epub 2015 Apr 13.
Novel fungicides are urgently needed. It was recently reported that the attachment of an octyl group at the O-4″ position of kanamycin B converts this antibacterial aminoglycoside into a novel antifungal agent. To elucidate the structure-activity relationship (SAR) for this phenomenon, a lead compound FG03 with a hydroxyl group replacing the 3″-NH2 group of kanamycin B was synthesized. FG03's antifungal activity and synthetic scheme inspired the synthesis of a library of kanamycin B analogues alkylated at various hydroxyl groups. SAR studies of the library revealed that for antifungal activity the O-4″ position is the optimal site for attaching a linear alkyl chain and that the 3″-NH2 and 6″-OH groups of the kanamycin B parent molecule are not essential for antifungal activity. The discovery of lead compound, FG03, is an example of reviving clinically obsolete drugs like kanamycin by simple chemical modification and an alternative strategy for discovering novel antimicrobials.
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