Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Search research articles

Related Experiment Videos

Side-product formation during cyclization with HBTU on a solid support

S C Story¹, J V Aldrich

¹Oregon State University, College of Pharmacy, Corvallis.

International Journal of Peptide and Protein Research

|March 1, 1994

Summary

This summary is machine-generated.

Related Concept Videos

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Alanine analogues of [D-Trp]CJ-15,208: novel opioid activity profiles and prevention of drug- and stress-induced reinstatement of cocaine-seeking behaviour.

British journal of pharmacology·2014

Same author

Zyklophin, a short-acting kappa opioid antagonist, induces scratching in mice.

Neuroscience letters·2014

Same author

Reinstatement of cocaine place-conditioning prevented by the peptide kappa-opioid receptor antagonist arodyn.

European journal of pharmacology·2007

Same author

Structure-activity relationships of arodyn, a novel acetylated kappa opioid receptor antagonist.

The journal of peptide research : official journal of the American Peptide Society·2005

Same author

An affinity label for delta-opioid receptors derived from [D-Ala2]deltorphin I.

The journal of peptide research : official journal of the American Peptide Society·2004

Same author

Synthesis and evaluation of potential affinity labels derived from endomorphin-2.

The journal of peptide research : official journal of the American Peptide Society·2002

The coupling reagent HBTU failed to form a strained lactam ring, instead producing unwanted tetramethylguanidinium (Tmg) derivatives. This limits HBTU

Area of Science:

Organic Chemistry
Peptide Chemistry
Solid-Phase Synthesis

Background:

Solid-phase peptide synthesis (SPPS) is crucial for creating complex peptides.
Lactam ring formation is a key step in synthesizing cyclic peptides.
HBTU is a common coupling reagent in peptide synthesis.

Purpose of the Study:

To investigate the utility of HBTU for synthesizing strained lactam rings on a solid support.
To characterize the byproducts formed during attempted lactamization using HBTU.
To assess the limitations of HBTU in specific cyclization reactions.

Main Methods:

Attempted solid-phase synthesis of a strained 10-membered lactam in [Dab2,D-Glu3,Leu5]enkephalinamide.
Characterization of reaction products using mass spectrometry, amino acid analysis, peptide sequencing, and NMR spectroscopy.

Related Experiment Videos

Main Results:

The attempted cyclization using HBTU failed to yield the desired lactam.
Major products identified were tetramethylguanidinium (Tmg) derivatives of the linear peptide.
Formation of Tmg derivatives resulted from the transfer of the tetramethyluronium moiety from HBTU to the Dab side chain.

Conclusions:

HBTU is not suitable for the formation of highly strained lactam rings via side-chain to side-chain cyclization.
The formation of Tmg byproducts significantly limits the application of HBTU in such synthetic strategies.
Alternative coupling reagents or strategies may be necessary for synthesizing strained lactams.