2591-98-2Relevant articles and documents
Palladium(II)-catalyzed oxidation of l-tryptophan by hexacyanoferrate(III) in perchloric acid medium: A kinetic and mechanistic approach
Fawzy, Ahmed
, p. 247 - 256 (2016)
The catalytic effect of palladium(II) on the oxidation of l-tryptophan by potassium hexacyanoferrate(III) has been investigated spectrophotometrically in aqueous perchloric acid medium. A first order dependence in [hexacyanoferrate(III)] and fractional-first order dependences in both [l-tryptophan] and [palladium(II)] were obtained. The reaction exhibits fractional-second order kinetics with respect to [H +]. Reaction rate increased with increase in ionic strength and dielectric constant of the medium. The effect of temperature on the reaction rate has also been studied and activation parameters have been evaluated and discussed. Initial addition of the reaction product, hexacyanoferrate(II), does not affect the rate significantly. A plausible mechanistic scheme explaining all the observed kinetic results has been proposed. The final oxidation products are identified as indole-3-acetaldehyde, ammonium ion and carbon dioxide. The rate law associated with the reaction mechanism is derived.
11-Step Total Synthesis of Araiosamines
Tian, Maoqun,Yan, Ming,Baran, Phil S.
, p. 14234 - 14237 (2016)
A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed, and their absolute configuration has been assigned. The dense array of functionality, high polarity, and rich stereochemistry coupled with equilibrating topologies present an unusual challenge for chemical synthesis and an opportunity for innovation. Key steps involve the use of a new reagent for guanidine installation, a remarkably selective C-H functionalization, and a surprisingly simple final step that intersects a presumed biosynthetic intermediate. Synthetic araiosamines were shown to exhibit potency against Gram-positive and -negative bacteria despite a contrary report of no activity.
Indolyl-3-acetaldoxime dehydratase from the phytopathogenic fungus Sclerotinia sclerotiorum: Purification, characterization, and substrate specificity
Pedras, M. Soledade C.,Minic, Zoran,Thongbam, Premila D.,Bhaskar, Vangala,Montaut, Sabine
, p. 1952 - 1962 (2010)
The purification and characterization of indolyl-3-acetaldoxime dehydratase produced by the plant fungal pathogen Sclerotinia sclerotiorum is described. The substrate specificity indicates that it is an indolyl-3-acetaldoxime dehydratase (IAD, EC 4.99.1.6), which catalyzes transformation of indolyl-3-acetaldoxime to indolyl-3-acetonitrile. The enzyme showed Michaelis-Menten kinetics and had an apparent molecular mass of 44 kDa. The amino acid sequence of IAD, determined using LC-ESI-MS/MS, identified it as the protein SS1G-01653 from S. sclerotiorum. IADSs was highly homologous (84% amino acid identity) to the hypothetical protein BC1G-14775 from Botryotinia fuckeliana B05.10. In addition, similarity to the phenylacetaldoxime dehydratases from Gibberella zeae (33% amino acid identity) and Bacillus sp. (20% amino acid identity) was noted. The specific activity of IADSs increased about 17-fold upon addition of Na2S2O4 under anaerobic conditions, but in the absence of Na2S2O 4 no significant change was observed, whether aerobic or anaerobic conditions were used. As with other aldoxime dehydratases isolated from microbes, the role of IADSs in fungal plant pathogens is not clear, but given its substrate specificity, it appears unlikely that IADSs is a general xenobiotic detoxifying enzyme.
S -indole benzamide derivative as well as preparation method and application thereof
-
, (2021/09/15)
S - Indole benzamide derivatives as well as a preparation method and application thereof relate to the technical field of pharmacy. The derivative has a structural formula. The specific preparation method comprises the following steps: taking indole as a starting raw material and performing acylation reaction. Reaction, oxidation reaction, (R)- (+) -tert-butylsulfenamide asymmetric synthesis reaction, hydrolysis reaction and acylation reaction to give the target product. By means of the method, a novel antiviral drug with a development prospect can be obtained, and the yield is high.
Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
Tan, Tong-De,Zhu, Xin-Qi,Jia, Mei,Lin, Yongjia,Cheng, Jun,Xia, Yuanzhi,Ye, Long-Wu
supporting information, p. 1309 - 1312 (2019/11/26)
An efficient gold-catalyzed anti-Markovnikov cycloisomerization-initiated tandem reaction of Boc-protected indole tethered homopropargyl amides has been achieved. This method delivers a wide range of valuable bridged aza-[n.2.1] skeletons (n = 3–7) at room temperature with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the gold-catalyzed tandem reaction of homopropargyl alcohol is also achieved to produce the bridged oxa-[3.2.1] skeleton.
Efficient Synthesis of the Peptide Fragment of the Natural Depsipeptides Jaspamide and Chondramide
Zarezin, Danil P.,Shmatova, Olga I.,Kabylda, Adil M.,Nenajdenko, Valentine G.
, p. 4716 - 4722 (2018/09/10)
A new method for the synthesis of the tripeptide part of the jaspamide and chondramide alkaloids using a Ugi reaction was developed. The reported approach is considerably shorter than all literature syntheses of the peptide parts of these natural products. A family of peptides with different substituents at the 2-position of the indole moiety was prepared to open up access to analogues of these natural products.
