Category: 106391-88-2

Asano, Akiko published the artcileEffect of the powerful plasticity of the tert-butyl side chain on the conformational equilibrium of ascidiacyclamides, Synthetic Route of 106391-88-2, the publication is Journal of Peptide Science (2021), 27(12), e3363, database is CAplus and MEDLINE.

Ascidiacyclamide [cyclo(-Ile1,5-oxazoline2,6-D-Val3,7-thiazole4,8-)2] is a cytotoxic cyclic peptide from ascidian. Through structural analyses using monosubstituted analogs (Xaa1: Ala, 2-aminobutyric acid, Val, cyclohexylglycine, and phenylglycine), we previously demonstrated the conformational equilibrium between its square and folded forms. As the bulkiness of the Xaa1 residue side chain was reduced, spontaneous folding was promoted, and the cytotoxicity decreased accordingly. In the present study, five disubstituted analogs in which a tert-leucine residue (Tle) was incorporated at the 5-position of the abovementioned monosubstituted analogs were synthesized, after which their structures were analyzed using X-ray diffraction, CD (CD) spectral measurements, and 1H NMR-based quant. anal. The side chains of the Tle and Ile residues are structural isomers of one another, and the Tle residue bearing the tert-Bu group can be expected to play a role as a building block. In fact, peptides incorporating Tle5 exhibited much less spontaneous folding than their Ile5 counterparts in both crystal and solution Increases in enthalpy and entropy due to the tert-Bu group during the folding process resulted in increased conformational free energy (ΔG°). The powerful plasticity of the tert-Bu group would stabilize the square form relating with cytotoxicity.

Journal of Peptide Science published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Synthetic Route of 106391-88-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dias, Luiz C. published the artcileChiral allylsilane additions to chiral N-Boc-α-amino aldehydes, Quality Control of 106391-88-2, the publication is Synlett (2000), 37-40, database is CAplus.

Addition of chiral allylsilane (S)-Me₃SiCH₂C(:CH₂)CHMeCH₂OCH₂Ph to chiral N-(tert-butoxycarbonyl) α-amino aldehydes in the presence of SnCl₄ in CH₂Cl₂ at -78° affords 1,2-syn homoallylic alcs., potential intermediates for the synthesis of hydroxyethylene peptide isosteres. The diastereoselectivity depends on the aldehyde absolute configuration, with (R)-α-amino aldehydes (matched case/anti-Felkin addition) exhibiting higher stereoselectivity than its enantiomer (mismatched case/Felkin addition).

Synlett published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Quality Control of 106391-88-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Lin, Geng-Jie published the artcileEnantiodivergent synthesis of trans-3,4-disubstituted succinimides by SmI₂-mediated Reformatsky-type reaction, HPLC of Formula: 106391-88-2, the publication is Tetrahedron Letters (2008), 49(25), 4007-4010, database is CAplus.

An enantiodivergent strategy for the synthesis of trans-3,4-disubstituted succinimides is reported. The key step is a highly trans-stereoselective SmI₂-induced Reformatsky-type reaction of 4-substituted O-benzoylated malimides with carbonyl compounds Double chirality transmissions were performed with good to excellent diastereoselectivities.

Tetrahedron Letters published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, HPLC of Formula: 106391-88-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Dullin, Anja published the artcileSynthesis and cytotoxicity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)-3-methylbutane]platinum(II) complexes, HPLC of Formula: 106391-88-2, the publication is ChemMedChem (2006), 1(6), 644-653, database is CAplus and MEDLINE.

A series of leaving group derivatives of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)-3-methylbutane]platinum(II) complexes were synthesized and tested for cytotoxicity. The enantiomeric purity was determined by ¹H NMR spectroscopy on the final diamines after derivation with (1R)-myrtenal. For coordination to platinum, the diamines were reacted with K₂Ptl₄. The treatment of diiodoplatinum(II) complexes (4F-Ph/iProp-Ptl₂) with Ag₂SO₄ resulted in the sulfatoplatinum(II) complexes (4F-Ph/iProp-PtSO₄), which can be easily transformed to dichloroplatinum(II) complexes (4F-Ph/iProp-PtCl₂) with 2 N HCl. The importance of the leaving groups and the configuration at the diamine ligand on the antiproliferative effects was evaluated on the hormone-dependent MCF-7 and the hormone-independent MDA-MB 231 breast cancer cell lines as well as the LNCaP/FGC prostate cancer cell line. (R,R)-4F-Ph/iProp-PtCl₂ was identified as the most active platinum(II) complex. The 3-Me group increased antiproliferative effects relative to the [1,2-diamino-1-(4-fluorophenyl)butane]platinum(II) complexes described in an earlier study.

ChemMedChem published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, HPLC of Formula: 106391-88-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Asano, Akiko published the artcileEffects of amino acids and chirality for molecular folding of desoxazoline-ascidiacyclamide derivatives: x-ray crystal structures of four cyclic octapeptides including unusual amino acids, cyclo(-Ile-aThr-D-Val-Thz-)₂, cyclo(-Ala-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), cyclo(-Val-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), and cyclo(-Ile-aThr-Val-Thz-Ile-aThr-D-Val-Thz-), Formula: C10H19NO3, the publication is Biopolymers (2001), 58(3), 295-304, database is CAplus and MEDLINE.

The desoxazoline derivative of ascidiacyclamide, cyclo(-L-Ile-L-allo-threonine-D-Val-thiazole-)₂ (1), was modified to disturb the C₂-symmetry. Three addnl. derivatives of ascidiacyclamide were prepared as follows: the Ile¹ residue of 1 was replaced with Ala (2) or Val (3), and the D-Val³ residue was replaced with Val (4). The crystal structures of 1-4 were analyzed by x-ray diffraction methods. The mols. of all compounds were folded and this type of structure has not been observed so far in x-ray structures of ascidiacyclamide derivatives except for patellamide D. The folding patterns of 1-4 were similar to each other and resembled that of patellamide. The asym. modifications at position 1 caused the conformational changes at local area, and these were related to peptide-peptide and peptide-solvent interactions. Despite the diverse backbone conformation generated by the epimeric modification at position 3, the entire mol. of 4 was folded. These results indicate that (1) the desoxazoline-ascidiacyclamides favored the folded structures, and (2) modifications of the side chain size at position 1 and the chirality at position 3 introduced the local conformational changes to the derivatives, suggesting that (3) the lack of the oxazoline block leads to conformational flexibility in 1-4, which accept the conformational change with no drastic change on the entire structure.

Biopolymers published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Formula: C10H19NO3.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Narita, Koichi published the artcileTotal Synthesis of the Bicyclic Depsipeptide HDAC Inhibitors Spiruchostatins A and B, 5”-epi-Spiruchostatin B, FK228 (FR901228) and Preliminary Evaluation of Their Biological Activity, Computed Properties of 106391-88-2, the publication is Chemistry – A European Journal (2009), 15(42), 11174-11186, S11174/1-S11174/103, database is CAplus and MEDLINE.

The bicyclic depsipeptide histone deacetylase (HDAC) inhibitors spiruchostatins A and B, 5”-epi-spiruchostatin B and FK228 were efficiently synthesized in a convergent and unified manner. The synthetic method involved the following crucial steps: (i) a Julia-Kocienski olefination of a 1,3-propanediol-derived sulfone and a L- or D-malic acid-derived aldehyde to access the most synthetically challenging unit, (3S or 3R,4E)-3-hydroxy-7-mercaptohept-4-enoic acid, present in a D-alanine- or D-valine-containing segment; (ii) a condensation of a D-valine-D-cysteine- or D-allo-isoleucine-D-cysteine-containing segment with a D-alanine- or D-valine-containing segment to directly assemble the corresponding seco-acids; and (iii) a macrocyclization of a seco-acid using the Shiina method or the Mitsunobu method to construct the requisite 15- or 16-membered macrolactone. The present synthesis has established the C5” stereochem. of spiruchostatin B. In addition, HDAC inhibitory assay and the cell-growth inhibition anal. of the synthesized depsipeptides determined the order of their potency and revealed some novel aspects of structure-activity relationships. It was also found that unnatural 5”-epi-spiruchostatin B shows extremely high selectivity (ca. 1600-fold) for class I HDAC1 (IC₅₀ = 2.4 nM) over class II HDAC6 (IC₅₀ = 3900 nM) with potent cell-growth-inhibitory activity at nanomolar levels of IC₅₀ values.

Chemistry – A European Journal published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Computed Properties of 106391-88-2.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Shengule, Sudhir R. published the artcileDiastereoselective Pictet-Spengler reactions of a tethered 2-aminoimidazole, Formula: C10H19NO3, the publication is Australian Journal of Chemistry (2014), 67(2), 184-191, database is CAplus.

The diastereoselective Pictet-Spengler reaction of aminopropyl-2-aminoimidazole with enantiopure aldehydes was investigated. With amino acid-derived aldehydes, anti-stereochem. was favored, with a diastereoselectivity up to 92% achievable. The absolute stereochem. of the products was determined through synthesis of a rigid derivative and from NMR data in combination with mol. modeling. The diastereoselectivity dependent on the steric bulk of the amino acid side chain and independent of the nitrogen protecting group. Lewis acids catalyzed the reaction but did not affect the diastereoselectivity.

Australian Journal of Chemistry published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C9H9NO, Formula: C10H19NO3.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Johnson, Erik P. published the artcilePreparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids, Safety of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Synthesis (2011), 4023-4026, database is CAplus.

A general method for the conversion of N-Boc (Boc = tert-butoxycarbonyl) amino acids into their homologated α-hydroxy-β-Fmoc (Fmoc = 9-fluorenylmethoxycarbonyl) amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrolysis of the nitrile group, followed by reprotection of the amino acid as the Fmoc derivative

Synthesis published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Safety of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Said, Ahmed M. published the artcileBinding cooperativity between a ligand carbonyl group and a hydrophobic side chain can be enhanced by additional H-bonds in a distance dependent manner: A case study with thrombin inhibitors, Application of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is European Journal of Medicinal Chemistry (2015), 405-424, database is CAplus and MEDLINE.

One of the underappreciated non-covalent binding factors, which can significantly affect ligand-protein binding affinity, is the cooperativity between ligand functional groups. Using four different series of thrombin inhibitors, we reveal a strong pos. cooperativity between an H-bond accepting carbonyl functionality and the adjacent P3 hydrophobic side chain. Adding an H-bond donating amine adjacent to the P3 hydrophobic side chain further increases this pos. cooperativity thereby improving the K_i by as much as 546-fold. In contrast, adding an amidine multiple H-bond/salt bridge group in the distal S1 pocket does not affect this cooperativity. An anal. of the crystallog. B-factors of the ligand groups inside the binding site indicates that the strong cooperativity is mainly due to a significant mutual reduction in the residual mobility of the hydrophobic side chain and the H-bonding functionalities that is absent when the separation distance is large. This type of cooperativity is important to encode in binding affinity prediction software, and to consider in SAR studies.

European Journal of Medicinal Chemistry published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Application of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Shibata, Makoto published the artcileTotal syntheses of patellamides, cytotoxic cyclic peptides from a marine tunicate, Recommanded Product: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Tennen Yuki Kagobutsu Toronkai Koen Yoshishu (1985), 267-74, database is CAplus.

The structures of patellamides A, B, and C have been proposed to be cyclic peptides I, II, and III, resp. I and II were synthesized by solution methods, but these synthetic peptides were not identical with natural patellamides B and C. An inspection of evidences used for the originally assigned structures and a synthetic study on the partial hydrolyzate of patellamide B indicated that the structures of patellamides B and C could be reassigned as cyclic peptides IV and V, resp., having the reverse order of amino acid residues. This deduction was confirmed by the syntheses of revised structures IV and V, which were completely identical with natural patellamides B and C, resp. The structures of patellamide A was analogously revised as cyclic peptide VI by its synthesis.

Tennen Yuki Kagobutsu Toronkai Koen Yoshishu published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C8H6ClN, Recommanded Product: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics