Morpholine, a strong contender for Fmoc removal in solid-phase peptide synthesis

被引：8

作者：

Mthembu, Sinenhlanhla N. ^{[1
,2
]}

Chakraborty, Amit ^{[1
]}

Schonleber, Ralph ^{[3
]}

Albericio, Fernando ^{[1
,4
,5
,6
]}

de la Torre, Beatriz G. ^{[1
,2
,6
]}

机构：

[1] Univ KwaZulu Natal, Sch Chem & Phys, Peptide Sci Lab, Durban, South Africa

[2] Univ KwaZulu Natal, Coll Hlth Sci, Sch Lab Med & Med Sci, KwaZulu Natal Res Innovat & Sequencing Platform KR, Durban, South Africa

[3] Bachem AG, Bubendorf, Switzerland

[4] Univ Barcelona, Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona, Spain

[5] Univ Barcelona, Dept Organ Chem, Barcelona, Spain

[6] Univ KwaZulu Natal, Sch Chem & Phys, Peptide Sci Lab, ZA-4000 Durban, South Africa

来源：

JOURNAL OF PEPTIDE SCIENCE | 2024年 / 30卷 / 02期

关键词：

aspartimide; diketopiperazine; Fmoc; side reactions; solid-phase peptide synthesis; ASPARTIMIDE FORMATION; PROTECTING GROUP; SIDE REACTIONS; GLYCOPEPTIDE; SPPS; PREVENTION; PIPERIDINE; ACID;

D O I：

10.1002/psc.3538

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Morpholine, which scores 7.5 in terms of greenness and is not a regulated substance, could be considered a strong contender for Fmoc removal in solid-phase peptide synthesis (SPPS). Morpholine in dimethylformamide (DMF) (50%-60%) efficiently removes Fmoc in SPPS, minimizes the formation of diketopiperazine, and almost avoids the aspartimide formation. As a proof of concept, somatostatin has been synthesized using 50% morpholine in DMF with the same purity as when using 20% piperidine-DMF.

引用

页数：11

共 63 条

[1] A backbone amide protecting group for overcoming difficult sequences and suppressing aspartimide formation [J].