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免疫佐剂糖肽MDP（N-乙酰基-胞壁酰-L-丙氨酰-D-异谷氨酰胺）一些新类似物的合成

Synthesis of some new analogs of the immunoadjuvant glycopeptide MDP (N-acetyl-muramyl-L-alanyl-D-isoglutamine).

作者信息

Lefrancier P, Derrien M, Lederman I, Nief F, Choay J, Lederer E

出版信息

Int J Pept Protein Res. 1978 Apr;11(4):289-96. doi: 10.1111/j.1399-3011.1978.tb02851.x.

DOI:10.1111/j.1399-3011.1978.tb02851.x
PMID:669885
Abstract

In our continued efforts to elucidate the relationship between the structure and the immunoadjuvant, antiinfectious or mitogenic activity of N-acetyl-muramyl-L-alanyl-D-isoglutamine (MDP), we report the synthesis of 11 new analogs. Five of them present some modifications in the N-acetyl-muramyl moiety.

摘要

在我们持续努力阐明N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺（MDP）的结构与免疫佐剂、抗感染或促有丝分裂活性之间关系的过程中，我们报道了11种新类似物的合成。其中5种在N-乙酰胞壁酰部分有一些修饰。

相似文献

1
Synthesis of some new analogs of the immunoadjuvant glycopeptide MDP (N-acetyl-muramyl-L-alanyl-D-isoglutamine).免疫佐剂糖肽MDP（N-乙酰基-胞壁酰-L-丙氨酰-D-异谷氨酰胺）一些新类似物的合成
Int J Pept Protein Res. 1978 Apr;11(4):289-96. doi: 10.1111/j.1399-3011.1978.tb02851.x.
2
Synthesis of N-acetyl-muramyl-L-alanyl-D-isoglutamine, an adjuvant of the immune response, and of some n-acetyl-muramyl-peptide analogs.免疫反应佐剂N-乙酰-胞壁酰-L-丙氨酰-D-异谷氨酰胺及一些N-乙酰-胞壁酰肽类似物的合成。
Int J Pept Protein Res. 1977;9(4):249-57. doi: 10.1111/j.1399-3011.1977.tb03488.x.
3
Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的碳水化合物类似物（位置、构型和旋光）的合成及其免疫佐剂活性。
Carbohydr Res. 1981 Aug 1;94(2):143-63. doi: 10.1016/s0008-6215(00)80713-2.
4
Non-specific MIF-like activity induced by the synthetic immunoadjuvant: N-acetyl muramyl-L-alanyl-D-isoglutamine (MDP).
Biochem Biophys Res Commun. 1978 Nov 29;85(2):684-90. doi: 10.1016/0006-291x(78)91216-0.
5
N-acetyl muramyl dipeptide stimulation of bone resorption in tissue culture.组织培养中N-乙酰胞壁酰二肽对骨吸收的刺激作用。
Infect Immun. 1982 Jan;35(1):133-7. doi: 10.1128/iai.35.1.133-137.1982.
6
Immunoadjuvant effects of the synthetic muramyl-dipeptide (MDP) N-acetylmuramyl-L-alanyl-D-isoglutamine.合成的胞壁酰二肽（MDP）N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的免疫佐剂作用。
Z Immunitatsforsch Immunobiol. 1978 Oct;155(1):87-92.
7
Absence of binding of MDP, a synthetic immunoadjuvant, to anti-peptidoglycan antibodies.合成免疫佐剂MDP与抗肽聚糖抗体无结合。
J Immunol. 1978 Oct;121(4):1219-22.
8
Chemical synthesis and adjuvant activity of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) analogs 1, 2.N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺（MDP）类似物1、2的化学合成及佐剂活性
Chem Pharm Bull (Tokyo). 1981 Jun;29(6):1644-54. doi: 10.1248/cpb.29.1644.
9
Higher immunoadjuvant activities of N-acetyl-beta-D-glucosaminyl-(1-4)-N-acetylmuramyl-L-alanyl-D-isoglutamine in comparison with N-acetylmuramyl-L-alanyl-D-isoglutamine.与N-乙酰基-胞壁酰-L-丙氨酰-D-异谷氨酰胺相比，N-乙酰-β-D-葡糖胺基-(1-4)-N-乙酰基胞壁酰-L-丙氨酰-D-异谷氨酰胺具有更高的免疫佐剂活性。
Microbiol Immunol. 1979;23(9):933-6. doi: 10.1111/j.1348-0421.1979.tb02828.x.
10
Correlation between in vivo anti-Pseudomonas and anti-Candida activities and clearance of carbon by the reticuloendothelial system for various muramyl dipeptide analogs, using normal and immunosuppressed mice.使用正常和免疫抑制小鼠，研究各种胞壁酰二肽类似物的体内抗假单胞菌和抗念珠菌活性与网状内皮系统碳清除率之间的相关性。
Infect Immun. 1982 Jan;35(1):105-10. doi: 10.1128/iai.35.1.105-110.1982.

引用本文的文献

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Structure-activity relationship in NOD2 agonistic muramyl dipeptides.NOD2 激动型 muramyl dipeptides 的结构-活性关系。
Eur J Med Chem. 2024 May 5;271:116439. doi: 10.1016/j.ejmech.2024.116439. Epub 2024 Apr 20.
2
Immunological castration of male mice by a totally synthetic vaccine administered in saline.通过在盐水中注射完全合成疫苗对雄性小鼠进行免疫去势。
Proc Natl Acad Sci U S A. 1982 Sep;79(17):5392-5. doi: 10.1073/pnas.79.17.5392.
3
Muramyl peptides. Variation of somnogenic activity with structure.胞壁酰肽。催眠活性随结构的变化。
J Exp Med. 1984 Jan 1;159(1):68-76. doi: 10.1084/jem.159.1.68.
4
Colony-stimulating activity induced by synthetic muramyl peptides: variation with chemical structure and association with anti-infectious activity.合成胞壁酰肽诱导的集落刺激活性：随化学结构的变化及与抗感染活性的关联
Infect Immun. 1984 Nov;46(2):495-500. doi: 10.1128/iai.46.2.495-500.1984.
5
Induction of antibodies directed against self and altered-self determinants by a synthetic adjuvant, muramyl dipeptide and some of its derivatives.一种合成佐剂、胞壁酰二肽及其某些衍生物诱导针对自身和改变的自身决定簇的抗体。
Immunology. 1980 Mar;39(3):441-50.