Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis

نویسندگان

  • Tobias M. Postma
  • Fernando Albericio
چکیده

Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1-3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Trimethoxyphenylthio as a Highly Labile Replacement for <italic>tert</italic>-Butylthio Cysteine Protection in Fmoc Solid Phase Synthesis

Trimethoxyphenylthio (S-Tmp) is described as a novel cysteine protecting group in Fmoc solid phase peptide synthesis replacing the difficult to remove tert-butylthio. S-Tmp and dimethoxyphenylthio (S-Dmp) were successfully used for cysteine protection in a variety of peptides. Moreover, both groups can be removed in 5min withmild reducing agents. S-Tmp is recommended for cysteine protection, as...

متن کامل

Microwave-assisted Solid-phase(SPPS) and Solution-phase (SPS) Synthesis of Biological Dipeptide ((β-alanine-L histidine)

Peptides have shown Promising effect as pharmaceutics with the potential to treat a widevariety of diseases. Peptides are mostly synthesized by biological technology or chemicalmethods. Solution phasepeptide synthesis (SPS) and solid phase peptide synthesis (SPPS) aretwo major chemical techniques for peptidesproduction.In this research, the synthesis ofdipeptde(β-alanine-L-histidine)wasexamined...

متن کامل

Synthesis of nocistatin C-terminal and it’s amide derivatives as an opioid peptide

A new biological active hexapeptide of C-terminal of nocistatin, contains Glu-Gln-Lys-Gln-Leu-Gln sequence was synthesized according to solid phase peptide synthesis on the surface of 2-chloro tritylchloride resin and using fmoc-protected amino acids in the presence of TBTU (O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyl uranium tetrafluoroborate) as a coupling reagent. Then, amidation of the C-te...

متن کامل

Automated synthesis of backbone protected peptides†

Solid phase peptide synthesis (SPPS) is a powerful technology for the chemical synthesis of peptides and small proteins. However, access to many targets is often complicated and sometimes precluded by the occurrence of so-called difficult sequences. When encountered during SPPS difficult sequences are associated with a collapse of the swollen resin volume, incomplete acylation and in the case o...

متن کامل

Nitrodibenzofuran: A One- and Two-Photon Sensitive Protecting Group That Is Superior to Brominated Hydroxycoumarin for Thiol Caging in Peptides

Photoremovable protecting groups are important for a wide range of applications in peptide chemistry. Using Fmoc-Cys(Bhc-MOM)-OH, peptides containing a Bhc-protected cysteine residue can be easily prepared. However, such protected thiols can undergo isomerization to a dead-end product (a 4-methylcoumarin-3-yl thioether) upon photolysis. To circumvent that photoisomerization problem, we explored...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 16  شماره 

صفحات  -

تاریخ انتشار 2014