(-)-(1S,4R)-4-[(t-Butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid - CAS 151907-79-8

Category
BOC-Amino Acids
Catalog number
BAT-006609
CAS number
151907-79-8
Molecular Formula
C11H17NO4
Molecular Weight
227.26
(-)-(1S,4R)-4-[(t-Butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylic acid
Synonyms
(-)-(1S,4R)-4-(Boc)aminocyclopent-2-enecarboxylic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.2±0.1 g/cm3
Melting Point
152.9 °C
Boiling Point
382.3°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H17NO4/c1-11(2,3)16-10(15)12-8-5-4-7(6-8)9(13)14/h4-5,7-8H,6H2,1-3H3,(H,12,15)(H,13,14)/t7-,8+/m1/s1
InChI Key
WOUNTSATDZJBLP-SFYZADRCSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC1CC(C=C1)C(=O)O
1.Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen.
Andolfi A1, Maddau L2, Cimmino A1, Linaldeddu BT2, Basso S1, Deidda A2, Serra S2, Evidente A3. Phytochemistry. 2014 Jul;103:145-53. doi: 10.1016/j.phytochem.2014.03.016. Epub 2014 Apr 23.
In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O-acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R*,2R*,3'S*,4'R*,5'R*)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, (1R*,2R*,3'S*,4'R*,5'R*,10'R*,12'R*,13'R*,14'S*) and (1R*,2R*,3'S*,4'R*,5'R*,10'S*,12'R*,13'R*,14'S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2-yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5).
2.[Chemical constituents from Cinnamomum cassia].
He S, Jiang Y, Tu PF. Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(18):3598-602.
Various column chromatography, such as silica gel, Sephadex LH-20, ODS, and semi-preparative HPLC was used to isolate and purify the chemical constituents from Cinnamomum cassia. The structures were determined on the basis of NMR and MS spectral data analysis, together with the comparison with literature data. Fifteen compounds were isolated from the 85% aqueous ethanol extract of C. cassia, and their structures were identified as (2R, 3R)-5,7,3',4'-tetramethoxyflavan-3-ol( 1), (2R, 3R)-5,7-dimethoxy-3',4'-methylenedioxyflavan-3-ol (2), coumarin (3), cinnamic acid (4), (E)-2-hydroxy-phenylpropionic acid cinnamoyl ester (5), 3, 3', 4, 4'-tetrahydroxy biphenyl (6), methylstictic acid (7), epi-boscialin (8), (1R,2S,3S,4S)-2,3-epoxy-1, 4-dihydroxy-5-methyl-5-cyelohexene (9), 4,5-dihydroxy-3-methyl cyclohex-2-enone (10), cis-4-hydroxymellein (11), and 2-hydroxy-4-methoxyl-cinnamaldehyde (12). Compounds 5-11 were obtained from this genus plants for the first time.
3.Cohaerins G-K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C-K.
Surup F1, Mohr KI, Jansen R, Stadler M. Phytochemistry. 2013 Nov;95:252-8. doi: 10.1016/j.phytochem.2013.07.027. Epub 2013 Aug 19.
Four azaphilones, for which the trivial names cohaerins G, H, I and K are proposed, were isolated from the methanolic stromatal extract of Annulohypoxylon cohaerens together with the known metabolites cohaerins C-F and 4,5,4',5'-tetrahydroxy-1,1'-binaphthyl (BNT). Their planar structures were determined by NMR spectroscopy and by mass spectrometry. While their core structure is identical with cohaerin C and F, respectively, subgroups 2-hydroxy-6-methylphenyl and (1R,2R,4S)-4-hydroxy-2-methyl-6-oxocyclohexyl account for the structural diversity as substituents at C-3 of the azaphilone core. The absolute stereochemistry was assigned by NOE NMR experiments, CD spectroscopy and derivatisation with Mosher's acid; in addition, the stereochemistry of cohaerins C-F was revised. The metabolites showed cytotoxic effects besides a weak antimicrobial activity.
4.Synthesis of a norcantharidin-tethered guanosine: Protein phosphatase-1 inhibitors that change alternative splicing.
Kwiatkowski S1, Sviripa VM1, Zhang Z2, Wendlandt AE2, Höbartner C3, Watt DS4, Stamm S5. Bioorg Med Chem Lett. 2016 Feb 1;26(3):965-8. doi: 10.1016/j.bmcl.2015.12.054. Epub 2015 Dec 18.
Phosphorylation and dephosphorylation of splicing factors play a key role in pre-mRNA splicing events, and cantharidin and norcantharidin analogs inhibit protein phosphatase-1 (PP1) and change alternative pre-mRNA splicing. Targeted inhibitors capable of selectively inhibiting PP-1 could promote exon 7 inclusion in the survival-of-motorneuron-2 gene (SMN2) and shift the proportion of SMN2 protein from a dysfunctional to a functional form. As a prelude to the development of norcantharidin-tethered oligonucleotide inhibitors, the synthesis a norcantharidin-tethered guanosine was developed in which a suitable tether prevented the undesired cyclization of norcantharidin monoamides to imides and possessed a secondary amine terminus suited to the synthesis of oligonucleotides analogs. Application of this methodology led to the synthesis of a diastereomeric mixture of norcantharidin-tethered guanosines, namely bisammonium (1R,2S,3R,4S)- and (1S,2R,3S,4R)-3-((4-(2-(((((2R,3R,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-yl)oxy)oxidophosphoryl)oxy)ethyl)-phenethyl)(methyl)carbamoyl)-7-oxabicyclo[2.
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