28426-51-9Relevant academic research and scientific papers
Total synthesis of wewakazole B
Long, Bohua,Zhang, Jingzhao,Tang, Xudong,Wu, Zhengzhi
supporting information, p. 9712 - 9715 (2016/10/31)
Wewakazole B is a novel cyclodecapeptide with highly potent cytotoxic activity isolated from a sample of M. producens collected from the Red Sea. It contains nine common and three modified amino acid residues. The first total synthesis of Wewakazole B was successfully achieved on a gram scale, unambiguously confirming its structure. Notable features include the careful choice of amino acid-protecting groups and the construction of three different substituted oxazoles present in this natural product.
Design, synthesis, and application of enantioselective coupling reagent with a traceless chiral auxiliary
Kolesinska, Beata,Kaminski, Zbigniew J.
supporting information; experimental part, p. 765 - 768 (2009/09/06)
(Chemical Equation Presented) Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure
Dynamic combinatorial libraries of hydrazone-linked pseudo-peptides: Dependence of diversity on building block structure and chirality
Liu, Jingyuan,West, Kevin R.,Bondy, Chantelle R.,Sanders, Jeremy K. M.
, p. 778 - 786 (2008/03/14)
Expanding on our earlier building block architecture [(MeO) 2CH-Linker-Pro-X-NHNH2 where X = Phe, Cha], we have produced a series of new pseudo-dipeptides [(MeO)2CH-Linker-Pro-X- NHNH2 where X = Val, Leu, Ile, A
Influence of solvent viscosity on the rate of hydrolysis of dipeptides by carboxypeptidase Y
Kanosue, Yoshifumi,Kojima, Satoshi,Ohkata, Katsuo
, p. 448 - 457 (2007/10/03)
The influence of solvent viscosity on the rate of enzymatic hydrolysis of a series of dipeptides (Z-Phe-Gly, Z-Phe-Sar, Z-Phe-Ala, Z-Phe-NMeAla, Z-Phe-Aib and Z-Phe-Pro) by carboxypeptidase Y was investigated. The effect of solvent viscosity on the enzymatic hydrolysis revealed that whereas all Kcat values decreased with viscosity, those of the N-alkyl peptides decreased more than those of the N-H peptides. The kinetic behaviour implies the involvement of conformational changes of the enzyme in terms of the 'induced-fit' process. Copyright
Relationship between the hydrophobicity of dipeptides and the Michaelis-Menten constant Km of their hydrolysis by carboxypeptidase-Y and carboxypeptidase-A
Kanosue, Yoshifumi,Kojima, Satoshi,Hiraga, Yoshikazu,Ohkata, Katsuo
, p. 1187 - 1193 (2007/10/03)
The enzymatic hydrolysis of dipeptides by carboxypeptidase-Y and carboxypeptidase-A was investigated. In the enzymatic hydrolysis of the dipeptides, a good linear relationship (r = 0.997 and 0.999) was found between the Michaelis-Menten constant (Km) and the hydrophobicity of the substrates evaluated from relative elution volume in reversed-phase HPLC. The correlation suggests that the hydrophobicity of the C-terminal amino acid is a major factor in governing the stability of the enzyme-substrate complex. The difference in the slope of the linear-regression lines seems to reflect the degree of relative hydrophobicity of the binding pockets in carboxypeptidase-Y and carboxypeptidase-A.
Polymer-supported DMI as a potential heterogeneous dehydrating agent: Application to esterification and amidation
Disadee, Wannaporn,Watanabe, Toshiko,Ishikawa, Tsutomu
, p. 115 - 117 (2007/10/03)
A new polymer-supported urea (P-DMI) (4) was prepared as a precursor for a new heterogeneous dehydrating agent, polymer-supported chloroamidinium chloride (P-DMC) (5). Application of 4 to esterification and amidation, after conversion to 5, efficiently af
Total synthesis and assignment of configuration of lissoclinamide 7
Wipf, Peter,Fritch, Paul C.
, p. 12358 - 12367 (2007/10/03)
The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline → thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.
KINETICS OF THE ALKALINE HYDROLYSIS OF SEVERAL N-BENZYLOXYCARBONYLDIPEPTIDE METHYL AND ETHYL ESTERS
Hoogwater, D. A.,Peereboom, M.
, p. 5325 - 5332 (2007/10/02)
The reaction rates of the alkaline hydrolysis of synthesized N-protected dipeptide methyl and ethyl esters were studied systematically.From the kinetic data the energies of activation, the pre-exponential factors and the reference values at 40 deg C were calculated.The rate of hydrolysis shows to be strongly dependent on the C-terminal amino acid in the sequence Gly >> Ala/Met/Phe > Leu >> Val/Pro.Surprisingly the N-terminal amino acid also exerts an effect, but in a different sequence.N-Terminal Phe in particular shows a relative accelerating effect.Remarkable is the significantly faster ester hydrolysis of glycine containing dipeptide ethyl esters in ethanol/water compared to the corresponding methyl esters in methanol/water.
Amino Acids and Peptides; 67. Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides
Schmidt, Ulrich,Kroner, Matthias,Beutler, Ulrich
, p. 475 - 477 (2007/10/02)
N-Benzyloxycarbonyl amino acid chlorides and α-benzyloxycarbonyloxy carboxylic acid chlorides are readily available by treating the corresponding carboxylic acids with 1-chloro-N,N,2-trimethyl-1-propen-1-amine.They can be immediately reacted with O-, N- and C-nucleophiles to afford peptides, ketones and esters.
