Fmoc-D-β-HomoThr(tBu)-OH
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Fmoc-D-β-HomoThr(tBu)-OH

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Category
Fmoc-Amino Acids
Catalog number
BAT-008456
CAS number
1217837-63-2
Molecular Formula
C24H29NO5
Molecular Weight
411.49
IUPAC Name
(3S,4S)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxy]pentanoic acid
Synonyms
2,3,5-Trideoxy-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-O-(2-methyl-2-propanyl)-L-threo-pentonic acid
Density
1.2±0.1 g/cm3
Boiling Point
602.3±55.0 °C at 760 mmHg
InChI
InChI=1S/C24H29NO5/c1-15(30-24(2,3)4)21(13-22(26)27)25-23(28)29-14-20-18-11-7-5-9-16(18)17-10-6-8-12-19(17)20/h5-12,15,20-21H,13-14H2,1-4H3,(H,25,28)(H,26,27)/t15-,21-/m0/s1
InChI Key
UFJMOCVIPRJMLW-BTYIYWSLSA-N
Canonical SMILES
CC(C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
1. Stereoselective Polymer-Supported Synthesis of Morpholine- and Thiomorpholine-3-carboxylic Acid Derivatives
Petra Králová, Veronika Fülöpová, Michal Maloň, Tereza Volná, Igor Popa, Miroslav Soural ACS Comb Sci. 2017 Mar 13;19(3):173-180. doi: 10.1021/acscombsci.6b00178. Epub 2017 Jan 30.
Herein we report the polymer-supported synthesis of 3,4-dihydro-2H-1,4-oxazine-3-carboxylic acid derivatives using immobilized Fmoc-Ser(tBu)-OH and Fmoc-Thr(tBu)-OH as the starting materials. After the solid-phase-synthesis of N-alkyl-N-sulfonyl/acyl intermediates, the target dihydrooxazines were obtained using trifluoroacetic acid-mediated cleavage from the resin. This approach was also studied for the preparation of dihydrothiazines from immobilized Fmoc-Cys(Trt)-OH. Inclusion of triethylsilane in the cleavage cocktail resulted in the stereoselective formation of the corresponding morpholine/thiomorpholine-3-carboxylic acids. Stereochemical studies revealed the specific configuration of the newly formed stereocenter and also the formation of stable N-acylmorpholine rotamers.
2. Polymer-Assisted Synthesis of Single and Fused Diketomorpholines
Petra Králová, Sandra Benická, Miroslav Soural ACS Comb Sci. 2019 Mar 11;21(3):154-157. doi: 10.1021/acscombsci.8b00176. Epub 2019 Jan 18.
The synthesis of different diketomorpholines via N-acyl-3,4-dihydro-2 H-1,4-oxazine-3-carboxylic acids is reported in this article. The key intermediates were prepared using a convenient solid-phase synthesis starting from polymer-supported Ser( tBu)-OH. After subsequent sulfonylation with 4-nitrobenzenesulfonyl chloride (4-Nos-Cl), alkylation with an α-bromoketone, cleavage of the 4-Nos group and acylation with an α-halocarboxylic acids, acid-mediated cleavage from the resin yielded dihydrooxazine-3-carboxylic acids in high crude purities. Depending on the reaction conditions, exposure to base resulted in cyclization to either oxazino[3,4- c][1,4]oxazine-diones or 3-methylidenemorpholine-2,5-diones. Further reaction with triethylsilane-trifluoroacetic acid (TES/TFA) led to olefin reduction, in the case of oxazino[3,4- c][1,4]oxazine-dione with full control of the newly formed stereocenter.
3. Photo-Curable Lacquer Sap Resin Based on Urushiol-Mimicking, Tyrosine-Containing Additive
Jiwon Park, Seon-Mi Jin, Avnish Kumar Mishra, Jung Ah Lim, Eunji Lee Langmuir. 2022 Aug 16;38(32):10010-10021. doi: 10.1021/acs.langmuir.2c01422. Epub 2022 Aug 7.
Oriental lacquer sap is attracting considerable attention as a renewable and eco-friendly natural resin with high durability, heat resistance, insulation, insect repellency, and antiseptic and antibacterial properties. However, to ensure excellent coating performance, it is necessary to improve the drying/curing process of lacquer sap with a time-consuming drying time at high humidity [relative humidity (RH), 70-90%] and ambient temperature (20-30 °C). Drawing on an understanding of the polymerization mechanism of urushiol, the main component of the lacquer sap consisted of a water-in-oil (W/O) emulsion, and this study presents an eco-friendly additive that mimics the structure-function of urushiol composed of a polar catechol head group and a nonpolar hydrocarbon tail. A photo-curable lacquer sap was thus developed by adding a tyrosine amino acid-based lipid agent (denoted as Y-ADDA), which allows faster and more effective drying/curing at lower humidity while maintaining the nature-derived properties of lacquer sap. Y-ADDA easily coassembles with urushiol in the W/O emulsion droplets, thereby significantly accelerating the formation of a polymer network along with urushiol during water evaporation leading to fast drying/curing under ultraviolet (UV) light irradiation at low humidity (~50% RH). The UV-cured lacquer sap resins showed higher performance in terms of film processing and physicochemical properties compared with that of the lacquer containing only tyrosine amino acids without aliphatic tail conjugation, N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-l-tyrosine Fmoc-Tyr(tBu)-OH. Furthermore, the drying and curing times, film morphology, transmittance, hardness, and adhesion strength of the UV-cured lacquer were markedly superior compared to those of shellac, a general eco-friendly fast-drying primer. The study provides useful strategies and insights to promote the industrial application of lacquer sap resins by employing biocompatible nanoagents developed with an understanding of the curing mechanism of natural resins and from the viewpoint of green and sustainable chemistry perspective.
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