Production Method for Cyclic Dipeptide Derived from Native Collagen

被引：7

作者：

Hayasaka, Fumitaka ^{[1
]}

Yamamoto, Shoko ^{[1
]}

Sakai, Yasuo ^{[1
]}

机构：

[1] Jellice Co Ltd, Cent Res Inst, 4-4-1 Sakae, Tagajo, Miyagi 9850833, Japan

来源：

FOOD SCIENCE AND TECHNOLOGY RESEARCH | 2016年 / 22卷 / 04期

关键词：

cyclo(-Gly-Pro); cyclic dipeptide; 2,5-diketopiperazine; collagen tripeptide; PEPTIDES; DIKETOPIPERAZINES; TRIPEPTIDE; ANALOGS;

D O I：

10.3136/fstr.22.477

中图分类号：

TS2 [食品工业];

学科分类号：

0832 ;

摘要：

In this study, a new method for producing cyclo(-Gly-Pro) using collagen as a raw material was examined. First, collagen was enzymatically hydrolysed and purified to obtain collagen tripeptide (CTP), rich in "GlyX-Y" tripeptides. After heating this product under atmospheric pressure in an aqueous solution at 95 degrees C for 24 h, purification was achieved by reverse-phase column chromatography. The isolated component was confirmed to be cyclo(-Gly-Pro) through structural analysis by MS and NMR spectroscopies. Purity was determined to be 93.6%, and the recovery rate from CTP was 22%, indicating that much Gly-Pro-Y in CTP contributed to cyclization. The cyclization rate from Gly-Pro-Hyp or Gly-Pro-Ala was much higher than that of Gly-Pro, suggesting that cyclo(-Gly-Pro) was efficiently generated from the Gly-Pro-Y sequence. In summary, this is a simple, practical manufacturing method for producing cyclo(-Gly-Pro) from collagen at low cost with high efficiency.

引用

页码：477 / 483

页数：7

共 17 条

[1] Enzymatic synthesis of dehydroderivatives from proline-containing cyclic dipeptides and their effects toward cell division [J].

Arunrattiyakorn, Panarat ;

Ikeda, Banri ;

Nitoda, Teruhiko ;

Kanzaki, Hiroshi .

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2007, 71 (03) :830-833

[2] SONICATION-ASSISTED CLEAVAGE OF HYDROPHOBIC PEPTIDES - APPLICATION IN MULTIPIN PEPTIDE-SYNTHESIS [J].

BRAY, AM ;

LAGNITON, LM ;

VALERIO, RM ;

MAEJI, NJ .

TETRAHEDRON LETTERS, 1994, 35 (48) :9079-9082

[3] Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine [J].

Bull, SD ;

Davies, SG ;

Moss, WO .

TETRAHEDRON-ASYMMETRY, 1998, 9 (02) :321-327

[4] A SYNTHESIS OF CYCLIC PEPTIDES UTILIZING HIGH MOLECULAR WEIGHT CARRIERS [J].

FRIDKIN, M ;

PATCHORN.A ;

KATCHALS.E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (20) :4646-&

[5] IGF-1 derived small neuropeptides and analogues: a novel strategy for the development of pharmaceuticals for neurological conditions [J].

Guan, Jian ;

Gluckman, Peter D. .

BRITISH JOURNAL OF PHARMACOLOGY, 2009, 157 (06) :881-891

[6] Identification of a novel endogenous memory facilitating cyclic dipeptide cyclo-prolylglycine in rat brain [J].

Gudasheva, TA ;

Boyko, SS ;

Akparov, VK ;

Ostrovskaya, RU ;

Skoldinov, SP ;

Rozantsev, GG ;

Voronina, TA ;

Zherdev, VP ;

Seredenin, SB .

FEBS LETTERS, 1996, 391 (1-2) :149-152

[7]

He HY, 1999, MED CHEM RES, V9, P424

[8] Structure-based exploration of cyclic dipeptide chitinase inhibitors [J].

Houston, DR ;

Synstad, B ;

Eijsink, VGH ;

Stark, MJR ;

Eggleston, IM ;

van Aalten, DMF .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (23) :5713-5720

[9] Diketopiperazines: biological activity and synthesis [J].

Martins, Maristela B. ;

Carvalho, Ivone .

TETRAHEDRON, 2007, 63 (40) :9923-9932

[10] Cyclo(Phe-Pro) modulates the expression of ompU in Vibrio spp. [J].

Park, DK ;

Lee, KE ;

Baek, CH ;

Kim, IH ;

Kwon, JH ;

Lee, WK ;

Lee, KH ;

Kim, BS ;

Choi, SH ;

Kim, KS .

JOURNAL OF BACTERIOLOGY, 2006, 188 (06) :2214-2221

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