High-Efficiency Solid Phase Peptide Synthesis (HE-SPPS)

被引：148

作者：

Collins, Jonathan M. ^{[1
]}

Porter, Keith A. ^{[1
]}

Singh, Sandeep K. ^{[1
]}

Vanier, Grace S. ^{[1
]}

机构：

[1] CEM Corp, Matthews, NC 28104 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 03期

关键词：

D O I：

10.1021/ol4036825

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of improvements to the standard solid phase peptide synthesis (SPPS) process allowing for significant gains in product purity along with only a 4 min standard cycle time and a 90% reduction in total waste produced is reported. For example, syntheses of the well-known (65-74)acyl carrier protein (ACP) and (1-42)beta-amyloid peptides were accomplished with 93 and 72% purity (UPLC-MS) in only 44 and 229 min, respectively.

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页码：940 / 943

页数：4

相关论文

共 18 条

[1] 9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP [J].

CARPINO, LA ;

HAN, GY .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) :3404-&

[2] ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[3]

Collins J. M., 2013, MICROWAVES ORGANIC S, V2, P897

[4]

Erdélyi M, 2002, SYNTHESIS-STUTTGART, P1592

[5] Nonthermal microwave effects revisited: On the importance of internal temperature monitoring and agitation in microwave chemistry [J].

Herrero, M. Antonia ;

Kremsner, Jennifer M. ;

Kappe, C. Oliver .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :36-47

[6] Synthesis and application of Nα-Fmoc-Nπ-4-methoxybenzyloxymethylhistidine in solid phase peptide synthesis [J].

Hibino, Hajime ;

Miki, Yasuyoshi ;

Nishiuchi, Yuji .

JOURNAL OF PEPTIDE SCIENCE, 2012, 18 (12) :763-769

[7] Fast conventional Fmoc solid-phase peptide synthesis with HCTU [J].

Hood, Christina A. ;

Fuentes, German ;

Patel, Hirendra ;

Page, Karen ;

Menakuru, Mahendra ;

Park, Jae H. .

JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (01) :97-101

[8] Nucleophilic Reactivities of Primary and Secondary Amines in Acetonitrile [J].

Kanzian, Tanja ;

Nigst, Tobias A. ;

Maier, Andreas ;

Pichl, Stefan ;

Mayr, Herbert .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (36) :6379-6385

[9] SOLID PHASE PEPTIDE SYNTHESIS .1. SYNTHESIS OF A TETRAPEPTIDE [J].

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2149-&

[10] Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis [J].

Palasek, Stacey A. ;

Cox, Zachary J. ;

Collins, Jonathan M. .

JOURNAL OF PEPTIDE SCIENCE, 2007, 13 (03) :143-148