Trends to Acid-Labile Cys Protecting Groups: Thp as an Efficient and Non-Aromatic Cys Protecting Group for Fmoc Chemistry

Ramos-Tomillero, Iván; Rodríguez, Hortensia; Alberício, Fernando

doi:10.17952/24aps.2015.274

Cited by 3 publications

(2 citation statements)

References 32 publications

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“…We began our protocol with N-Boc-L-serine (Boc means t-butyloxy carbonyl, as shown in Scheme 1), with the chiral center being retained until the end product. The hydroxyl in 6 was protected by tetrahydropyran (THP) because THP can exist stably in the presence of a strong base or reducing agent during the synthesis process [12]. Carboxylic acid 6 was converted into an amide under the action of 1,1'-Carbonyldiimidazole (CDI) and ammonia to give 7.…”

Section: Resultsmentioning

confidence: 99%

Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

Liu¹,

Kai

et al. 2023

Molecules

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Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of Orychophragmus violaceus was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid structure, the main block of orychophragine D is constructed of an oxotriazine and an oxopiperazine, which are connected in parallel by a C-N bond. In this paper, a preparation method for the novel heterocycle skeleton of orychophragine D is proposed for the first time. N-Boc-L-serine was utilized as the original material to complete the preparation with 11 steps in a 13% overall yield. A hydroxyl group was established on the side chain of the skeleton as the reaction site for researchers to conduct further structural modification or derivatization.

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Section: Resultsmentioning

confidence: 99%

Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

Liu¹,

Kai

et al. 2023

Molecules

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“…Like TFA-labile protecting groups Trt and Dpm, Thp can be easily removed by TFA in the presence of scavengers. ,, Cys S -Thp protection is fully compatible with Fmoc-based SPPS. Cys(Thp) used in peptide synthesis produces diastereomeric mixture of products as the carbon atom of Thp involved in thioether linkage with the Cys thiol generates a chiral center.…”

Section: Acid Labile Protecting Groupsmentioning

confidence: 99%

Ready to Use Cysteine Thiol Protecting Groups in SPPS, A Practical Overview

Chakraborty,

Mthembu,

de la Torre

et al. 2024

Org. Process Res. Dev.

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Protecting group chemistry plays a pivotal role during peptide synthesis. For the synthesis of cysteinyl peptides, this is more significant as cysteine (Cys) is involved in the formation of two key peptide bonds�the amide and the disulfide. Cys also poses itself as one of the most sensitive amino acid residues during peptide synthesis, especially for the occurrence of side reactions such as racemization, elimination, alkylation, etc. The magnitude of these side reactions is dependent on several factors including the choice of appropriate protecting groups for Cys thiol. The regioselective synthesis of multidisulfide peptides is a sequential process and it requires different sets of Cys thiol protections with unique removal conditions for each set of protecting groups used. Here, the selection of Cys side-chain protections is significant in obtaining the final peptide with the desired conformation and a good yield. With the proper knowledge of the chemistry of Cys thiol protecting groups trouble-free synthesis of multicysteinyl peptides can be achieved with minimization/elimination of a plethora of side reactions related to Cys thiol. In this current review, ready to use/commercialized Cys thiol protecting groups have been discussed with a focus on their use for the synthesis of multidisulfide peptides.

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Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

et al. 2017

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Tetrahydropyranyl (Thp) is recognized as a useful protecting group for alcohols in organic synthesis. It has several advantages, including low cost, ease of introduction, general stability to most non‐acidic reagents, it confers good solubility, and the ease with which it can be removed if the functional group it protects requires manipulation. However, little attention has been paid to Thp in peptide chemistry. Provided here is a concise analysis of the Thp protection of various amino acid functionalities (OH, SH, NH and COOH) and its application to peptide synthesis. Thp is a useful moiety for the side‐chain protection of serine, threonine and cysteine and is suitable for the Fmoc/tBu solid‐phase peptide synthesis strategy. The immobilized version of 3,4‐dihydro‐2H‐pyran, the so‐called Ellman resin, is also discussed as a useful solid support for anchoring the side chains of serine, threonine and tryptophan residues.

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Trends to Acid-Labile Cys Protecting Groups: Thp as an Efficient and Non-Aromatic Cys Protecting Group for Fmoc Chemistry

Cited by 3 publications

References 32 publications

Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

Ready to Use Cysteine Thiol Protecting Groups in SPPS, A Practical Overview

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

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