Peptide efficiency

LA Carpino. l-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive. J Am Chem Soc 115, 4397, 1993. 

V Dourtoglou, J-C Ziegler, B Gross. L hexafluorophosphate de O-benzotriazolyl-AW-tetramethyluronium hexafluorophosphate a new and efficient peptide coupling reagent. Tetrahedron Lett 1269, 1978. 

T Miyazawa, T Otomatsu, Y Fukui, T Yamada, S Kuwata. Racemization-free and efficient peptide synthesis by the carbodiimide method using 1-hydroxybenzotriazole and copper(II) chloride simultaneously as additives. J Chem Soc Chem Commun 419, 1988. 

Beside borosilicate and fused silica capillaries, PS/DVB monoliths have been fabricated within the confines of steel and PEEK tubings [52]. In order to increase the hydrophobic character of the supports, a Friedel-Crafts alkylation reaction was used for the attachment of Cig-moieties to the polymer surface. The derivatized material was demonstrated to be more retentive and to provide more efficient peptide separations compared with the original, nonderivatized monolith. 

This type of chemistry has not been developed further into an efficient peptide synthesis involving A-terminal addition of amino acid residues to peptide esters. The main problems are concerned with the removal of the synthesized peptide from the cobalt(III) ion without causing racemization of chiral centres or hydrolysis of peptide linkages. 

An inherent drawback of this methodology is that quantitative information is only obtained from those peptides which are subjected to MS/MS analysis. This fact stresses the necessity for efficient peptide separation via multidimensional chromatography (e.g., SCX/reversed-phase HPLC) prior to tandem MS analysis. Moreover, ion trap instruments cannot be employed in quantitative iTRAQ experiments since their peptide fragmentation spectra do not contain information... 

In common with other application areas of chromatographic separation, a considerable amount of effort has been expended recently on the development of different elution conditions and types of stationary phases for peptide separations in attempts to maximize column selectivities without adversely affecting column efficiences. Peptide retention will invariably be mediated by the participation of electrostatic, hydrogen bonding, and hydrophobic interactions in the distribution phenomenon. The nature of the predominant distribution mechanism will be dependent on the physical and chemical characteristics of the stationary phase as well as the nature of the molecular forces which hold the solute molecules within the mobile and stationary zones. The retention of the solute in all HPLC modes can be described by the equation... 

Carpino LA. 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupUng additive. J. Am. Chem. Soc. 1993 115 4397-4398. Roberston N, Ramage R. Racemisation studies of a novel coupling reagent for solid phase peptide synthesis. Tetrahedron 1999 55 2713-2720. 

For efficient peptide bond formation acid halides azides 2,b l and Leuchs anhydridesb l were employed as the first activated species in peptide synthesis. Since then, besides considerable improvements to the azide (see Section 3.1) as well as the V-carboxyanhydride 7 procedure d (sgg Section 3.4.3), the methods have evolved over decades along a few basic principles as outlined in Scheme 2. The symmetrical the mixed carboxylic acid 4,b 5s] and the carbonic acid anhydrides were developed and remain useful despite the... 

The use of symmetrical anhydrides for the synthesis of peptides in solution has not found widespread application, although a number of efficient peptide syntheses have been performed using this procedure.Preparation and use of synunetrical anhydrides for peptide synthesis in solution has been comprehensively reviewed. ... 

Ivanov, A. R., Horvath, C. and Karger, B. L. High-efficiency peptide analysis on monolithic multi-mode capillary columns Pressure-assisted capillary electrochromatography/capillary electrophoresis coupled to UV and electrospray ionization-mass spectrometry. Electrophoresis, 24,3663, 2003. 

Zhang, H.M., Kazazic, S., Schaub, T.M., et al. (2008) Enhanced digestion efficiency, peptide ionization efficiency, and sequence resolution for protein hydrogen/deuterium exchange monitored by Fourier tians-form ion cyclotron resonance mass spectrometry. Analytical Chemistry, 80 (23), 9034-9041. 

Ivanov AR, Horvath C, Karger BE (2003) High-efficiency peptide analysis on monolithic multimode... 

Katayama, H., Hojo, H., Ohira, T., and Nakahara, Y. (2008) An efficient peptide ligation using azido-protected peptides via the thioester method. Tetrahedron Letters, 49, 5492-5494. 

---