Practical synthesis of peptide C-terminal aldehyde on a solid support

Konno, Hiroyuki; Sema, Yoshihiro; Ishii, Manabu; Hattori, Yoshiyuki; Nosaka, Kazuto; Akaji, Kenichi

doi:10.1016/j.tetlet.2013.06.103

Cited by 9 publications

(5 citation statements)

References 20 publications

(15 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In contrast to standard SPPS, we intended to prepare a peptide‐linker aldehyde 14 that would undergo reductive amination after its cleavage from the resin. Konno et al reported the preparation of similar peptides on solid support, but obtained epimers for the amino acid bearing the aldehyde functionality. However, this problem was impossible for our synthetic route because of the propyl linker between the first amino acid and the aldehyde functionality.…”

Section: Resultsmentioning

confidence: 99%

Solid Phase‐Supported Synthesis of Muraymycin Analogues

2019

View full text Add to dashboard Cite

Naturally occurring muraymycin nucleoside antibiotics represent a promising class of novel antimicrobials as they inhibit MraY, an enzyme involved in bacterial cell wall biosynthesis. The synthesis of muraymycins and their analogues is challenging as it involves multi‐step routes, thus hampering detailed structure‐activity relationship (SAR) studies. In this work, we report a novel solid phase‐based synthetic strategy for accessing muraymycin analogues via a modular approach, thereby enabling a more efficient access to structural variations, particularly of the muraymycin peptide moiety. The efficiency of this new method was exemplified in an alanine scan of the peptide unit. The inhibitory in vitro activities of the resultant analogues towards MraY provided novel SAR insights. Overall, this new synthetic method for the preparation of muraymycin analogues might support the development of these antibacterial agents towards potential drug candidates.

show abstract

Section: Resultsmentioning

confidence: 99%

Solid Phase‐Supported Synthesis of Muraymycin Analogues

2019

View full text Add to dashboard Cite

show abstract

“…Thus, although ketones and aldehyde usually are not typical functional group of peptides, many procedures have been developed to install this group on peptidic structures. [56,57,58] Generally, oxime and hydrazone formation can be considered as a single type of conjugation reaction, as they are very similar functional groups; however, oximes have been demonstrated to be more stable than hydrazones. [59] Oxime/hydrazone ligation can be conducted both in aqueous and organic solvents, without metal catalysts; they generally show high selectivity and compatibility with other functional groups in PDCs chemistry.…”

Section: Reactions Involving Carbonyl Groupsmentioning

confidence: 99%

“…Carbonyl groups can easily condense with oxyamino group, yielding oximes, or with hydrazines, giving hydrazone functionalities. Thus, although ketones and aldehyde usually are not typical functional group of peptides, many procedures have been developed to install this group on peptidic structures [56,57,58] . Generally, oxime and hydrazone formation can be considered as a single type of conjugation reaction, as they are very similar functional groups; however, oximes have been demonstrated to be more stable than hydrazones [59] …”

Section: Conjugation Reactionsmentioning

confidence: 99%

A Brief Guide to Preparing a Peptide–Drug Conjugate

Bugatti

2023

ChemBioChem

View full text Add to dashboard Cite

Peptide–drug conjugates (PDCs) have recently emerged as interesting hybrid constructs not only for targeted therapy, but also for the early diagnosis of different pathologies. In most cases, the crucial step in the PDC synthesis is the final conjugation step, where a specific drug is bound to a particular peptide‐/peptidomimetic‐targeting unit. Thus, this concept paper aims to give a short guide to determining the finest conjugation reaction, by considering in particular the reaction conditions, the stability of the linker and the major pros and cons of each reaction. Based on the recent PDCs reported in literature, the most common and efficient conjugation methods will be systematically presented and compared, generating a short guide to consult while planning the synthesis of a novel peptide–drug conjugate.

show abstract

“…Tokaramide A, 35) isolated from the marine sponge Theonella mirabilis, was successfully synthesized by this acetal-thioacetal conversion procedure and by the reduction of Weinreb amide bound to the solid support. 36,37) As for the design and evaluation of low-molecularweight peptide-based severe acute respiratory syndrome (SARS) chymotrypsin-like (3CL) protease inhibitors, SARS is a contagious respiratory disease in humans caused by the SARS coronavirus (SARS-CoV). [38][39][40] SARS 3CL protease is a cysteine protease containing a Cys-His catalytic dyad, that cleaves precursor poly proteins at as many as 11 conserved sites involving a conserved Gln at the P1 position and a small amino acid (Ser, Ala, or Gly) at the P 0 1 position.…”

Section: Synthesis and Evaluation Of Peptide Aldehyde-type Inhibimentioning

confidence: 99%