Fmoc-L-isoleucinol
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Fmoc-L-isoleucinol

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Category
Amino Alcohol
Catalog number
BAT-002613
CAS number
133565-46-5
Molecular Formula
C21H25NO3
Molecular Weight
339.4
Fmoc-L-isoleucinol
Synonyms
Fmoc-L-isoleucinol; (9H-Fluoren-9-yl)methyl ((2S,3S)-1-hydroxy-3-methylpentan-2-yl)carbamate
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.149 g/cm3
Melting Point
122-128 °C
Boiling Point
525.204ºC at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H25NO3/c1-3-14(2)20(12-23)22-21(24)25-13-19-17-10-6-4-8-15(17)16-9-5-7-11-18(16)19/h4-11,14,19-20,23H,3,12-13H2,1-2H3,(H,22,24)/t14-,20+/m0/s1
InChI Key
YMPMFRNXDNCNRH-VBKZILBWSA-N
Canonical SMILES
CCC(C)C(CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. Total Synthesis of L-156,373 and an oxoPiz Analogue via a Submonomer Approach
Yassin M Elbatrawi, Chang Won Kang, Juan R Del Valle Org Lett. 2018 May 4;20(9):2707-2710. doi: 10.1021/acs.orglett.8b00912. Epub 2018 Apr 18.
The first chemical synthesis of L-156,373 (1), a potent oxytocin receptor antagonist isolated from Streptomyces silvensis, is reported. Assembly of the unusual d-Piz-l-Piz dipeptide subunit was achieved through a sequential electrophilic amination-acylation-deprotection strategy followed by late-stage Piz ring formation. Synthesis and incorporation of a novel N-hydroxy-l-isoleucine building block is also described. This submonomer approach was further applied to the expedient synthesis of a di-δ-oxopiperazic acid analogue of 1 starting from Fmoc-Glu( tBu)-OH building blocks.
2. Tuneable Hybrid Hydrogels via Complementary Self-Assembly of a Bioactive Peptide with a Robust Polysaccharide
Kate Firipis, et al. ACS Biomater Sci Eng. 2021 Jul 12;7(7):3340-3350. doi: 10.1021/acsbiomaterials.1c00675. Epub 2021 Jun 14.
Synthetic materials designed for improved biomimicry of the extracellular matrix must contain fibrous, bioactive, and mechanical cues. Self-assembly of low molecular weight gelator (LMWG) peptides Fmoc-DIKVAV (Fmoc-aspartic acid-isoleucine-lysine-valine-alanine-valine) and Fmoc-FRGDF (Fmoc-phenylalanine-arginine-glycine-aspartic acid-phenylalanine) creates fibrous and bioactive hydrogels. Polysaccharides such as agarose are biocompatible, degradable, and non-toxic. Agarose and these Fmoc-peptides have both demonstrated efficacy in vitro and in vivo. These materials have complementary properties; agarose has known mechanics in the physiological range but is inert and would benefit from bioactive and topographical cues found in the fibrous, protein-rich extracellular matrix. Fmoc-DIKVAV and Fmoc-FRGDF are synthetic self-assembling peptides that present bioactive cues "IKVAV" and "RGD" designed from the ECM proteins laminin and fibronectin. The work presented here demonstrates that the addition of agarose to Fmoc-DIKVAV and Fmoc-FRGDF results in physical characteristics that are dependent on agarose concentration. The networks are peptide-dominated at low agarose concentrations, and agarose-dominated at high agarose concentrations, resulting in distinct changes in structural morphology. Interestingly, at mid-range agarose concentration, a hybrid network is formed with structural similarities to both peptide and agarose systems, demonstrating reinforced mechanical properties. Bioactive-LMWG polysaccharide hydrogels demonstrate controllable microenvironmental properties, providing the ability for tissue-specific biomaterial design for tissue engineering and 3D cell culture.
3. FMOC-amino acid surfactants: discovery, characterization and chiroptical spectroscopy
R Vijay, Prasad L Polavarapu J Phys Chem A. 2012 Nov 8;116(44):10759-69. doi: 10.1021/jp308134m. Epub 2012 Oct 25.
The sodium salts of amino acids with hydrophobic fluorenyl methyloxy carbonyl (FMOC) group and short alkyl side chains are found to have surfactant properties. This was ascertained first through visual observation of concentration dependent solution behavior and then confirmed by tensiometry measurements. The critical micelle concentrations (CMCs) for the sodium salts of FMOC-l-valine, FMOC-L-leucine, and FMOC-L-isoleucine have been determined to be ~0.1 M. The sodium salt of FMOC-l-norleucine forms a gel at >0.2 M. Powder X-ray diffraction measurements indicated that these surfactants adopt bilayer structures. Three different chiroptical spectroscopic properties, namely optical rotation, electronic circular dichroism, and vibrational circular dichroism, are presented for these surfactants. The specific rotation is found to exhibit an unprecedented increase with concentration beyond CMC. This observation opens up a new area of research relating the concentration dependent increase in specific rotation to the size and shape of aggregates formed by the surfactants.
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