Synthesis of N-Trityl-L-homoserine

Attention is called on the extreme simple procedure for N-protection of amino acids mediated through previous silylation. Although the methodology is known, it has rather scarcely been used. Some examples show the versatility of a one-pot procedure. Selective BOC and 2-Na-protections of His were also worked out. INTRODUCTIONAlthough N-silylated species of amino acids and peptides have been occasionaly used for the preparation of the corresponding N-urethanes (1) and -acyl derivatives (2) this approach seems not to be generally applied, i.a. because of the fact that the silyl derivatives are generally formed ex-tempore. In view of the extreme sensitivity to hydrolysis and the rather restricting conditions for their preparation, the procedure does not in general offer advantages above the classical procedures, e.g. using Schotten-Baumann conditions. A major draw back of the latter method however is, that often parasite activation of the carboxyl function results in peptide formation (16), unless separate steps including previous esterification would be used. We found that the N,O-bis silylated amino acids or peptide acids can easily be prepared through in-situ silylation using trimethylsilyl cyanide (TMS-CN) ( 3 ) and that even a large excess of the agent, often used as cosolvent, can safely be applied, so that even amine salts of these components become effectively silylated, especially at the free carboxyl terminus. The in-situ formed silyl esters are unreactive towards strong acylating agents (e.g. of the type RCOX; X = C1, Br, F, RCO), so that the carboxyl groupings become effectively protected. After reaction at the amino side, any excess of reagents can easily be removed, so that a one-pot procedure usually results in the desired N-derivatization in high yield and high purity. During the preparation of this contribution a similar strategy for specific N-acylation and urethane formation (using TMS-Clfbase) and avoiding oligomerization has been reported by Meienhofer e.a. (17) but the silylation by TMS-CN offers definitive advantages ( 3 ) .

show abstract

One Pot N‐Protection of Amino Acids

Becu

Reyniers

Anteunis

et al. 1990

Bulletin des Soc Chimique

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: SYNTHESIS OF N‐TRITYL‐L‐HOMOSERINE

Barlos¹,

Theodoropoulos²

1982

Chemischer Informationsdienst

View full text Add to dashboard Cite

show abstract

Anwendung von N‐Tritylaminosäure‐(1‐benzotriazolylestern) bei der Synthese von Peptiden

1984

View full text Add to dashboard Cite

Der synthetische Nutzen von N‐Tritylaminosäure‐(1‐benzotriazolylestern) 2 beim Aufbau von Peptiden‐wird am Beispiel von Leucin‐Enkephalin (18) und Leucin‐Enkephalinamid (19) untersucht. Die Synthese wird in Lösung und an Festkörpern durchgeführt. Neue spektrophotometrische Meßmethoden, die auf der leichten Abspaltbarkeit der N‐Trityl‐Gruppe basieren und bei denen die Absorption des frei gewordenen Triphenylmethanols bestimmt wird, dienen zur Verfolgung der Verknüpfungsschritte und zur Bestimmung der freien Aminogruppen am Festkörper.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of N-Trityl-L-homoserine

Cited by 9 publications

References 10 publications

One Pot N‐Protection of Amino Acids

One Pot N‐Protection of Amino Acids

ChemInform Abstract: SYNTHESIS OF N‐TRITYL‐L‐HOMOSERINE

Anwendung von N‐Tritylaminosäure‐(1‐benzotriazolylestern) bei der Synthese von Peptiden

Contact Info

Product

Resources

About