N36, HR1, gp41 HIV Fragment_Ac-Ser-Gly-Ile-Val-Gln-Gln-Gln-Asn-Asn-Leu-Leu-Arg-Ala-Ile-Glu-Ala-Gln-Gln-His-Leu-Leu-Gln-Leu-Thr-Val-Trp-Gly-Ile-Lys-Gln-Leu-Gln-Ala-Arg-Ile-Leu-CONH2_Ac-SGIVQQQNNLLRAIEAQQHLLQLTVWGIKQLQARIL-CONH2_人类免疫缺陷病(HIV)肽

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N36, HR1, gp41 HIV Fragment

编号：407301

CAS号：

单字母：Ac-SGIVQQQNNLLRAIEAQQHLLQLTVWGIKQLQARIL-CONH2

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编号:	407301
中文名称:	N36, HR1, gp41 HIV Fragment
单字母:	Ac-SGIVQQQNNLLRAIEAQQHLLQLTVWGIKQLQARIL-CONH2
三字母:	Ac N端乙酰化封端 -Ser L-丝氨酸：serine。系统命名为(2S)-氨基-3-羟基丙酸。是编码氨基酸。因可从蚕丝中获得而得名。符号：S，Ser。在丝原蛋白及某些抗菌素中含有 D-丝氨酸。 -Gly 甘氨酸：glycine。系统命名为 2-氨基乙酸。是编码氨基酸中没有旋光性的最简单的氨基酸，因具有甜味而得名。符号：G，Gly。 -Ile L-异亮氨酸：isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子，是哺乳动物的必需氨基酸。符号:I，Ile。 -Val L-缬氨酸：valine。系统命名为(2S)-氨基-3-甲基丁酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：V，Val。在某些放线菌素如缬霉素中存在 D-缬氨酸。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Asn 天冬酰胺：asparagine。L-天冬酰胺的系统命名为(2S)-氨基-3-氨酰基丙酸，是编码氨基酸。符号：N，Asn。D-天冬酰胺存在于短杆菌肽A分子中。 -Asn 天冬酰胺：asparagine。L-天冬酰胺的系统命名为(2S)-氨基-3-氨酰基丙酸，是编码氨基酸。符号：N，Asn。D-天冬酰胺存在于短杆菌肽A分子中。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Arg L-精氨酸：arginine。系统命名为(2S)-氨基-5-胍基戊酸。在生理条件下带正电荷，为编码氨基酸。是幼小哺乳动物的必需氨基酸。符号：R，Arg。 -Ala 丙氨酸：alanine。L-丙氨酸的系统命名为(2S)-氨基丙酸，是编码氨基酸，也叫L-α-丙氨酸。符号：A，Ala。D-丙氨酸存在于多种细菌细胞壁的糖肽中。β-丙氨酸是维生素泛酸和辅酶A的组分。 -Ile L-异亮氨酸：isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子，是哺乳动物的必需氨基酸。符号:I，Ile。 -Glu L-谷氨酸：glutamic acid。系统命名为(2S)-氨基-戊二酸。是编码氨基酸。符号：E，Glu。D-谷氨酸存在于多种细菌的细胞壁和某些细菌杆菌肽中。 -Ala 丙氨酸：alanine。L-丙氨酸的系统命名为(2S)-氨基丙酸，是编码氨基酸，也叫L-α-丙氨酸。符号：A，Ala。D-丙氨酸存在于多种细菌细胞壁的糖肽中。β-丙氨酸是维生素泛酸和辅酶A的组分。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -His L-组氨酸：histidine。系统命名为(2S)-氨基-3-(4-咪唑基)丙酸。其侧链带有弱碱性的咪唑基，为编码氨基酸。是幼小哺乳动物的必需氨基酸。符号：H，His。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Thr L-苏氨酸：threonine。系统命名为(2S)-氨基-(3R)-羟基丁酸。有两个手性中心，是编码氨基酸。是哺乳动物的必需氨基酸。符号：T，Thr。 -Val L-缬氨酸：valine。系统命名为(2S)-氨基-3-甲基丁酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：V，Val。在某些放线菌素如缬霉素中存在 D-缬氨酸。 -Trp L-色氨酸：tryptophan[e]。系统命名为(2S)-氨基-3-(3-吲哚基)丙酸。是编码氨基酸，哺乳动物的必需氨基酸。符号：W，Trp。某些抗菌素中含有 D-色氨酸。 -Gly 甘氨酸：glycine。系统命名为 2-氨基乙酸。是编码氨基酸中没有旋光性的最简单的氨基酸，因具有甜味而得名。符号：G，Gly。 -Ile L-异亮氨酸：isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子，是哺乳动物的必需氨基酸。符号:I，Ile。 -Lys L-赖氨酸：lysine。系统命名为(2S)-6-二氨基已酸。是编码氨基酸中的碱性氨基酸，哺乳动物的必需氨基酸。在蛋白质中的赖氨酸可以被修饰为多种形式的衍生物。符号：K，Lys。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -Gln L-谷氨酰胺：glutamine。系统命名为(2S)-氨基-4-氨酰基丁酸，是编码氨基酸。符号：GIn，Q。 -Ala 丙氨酸：alanine。L-丙氨酸的系统命名为(2S)-氨基丙酸，是编码氨基酸，也叫L-α-丙氨酸。符号：A，Ala。D-丙氨酸存在于多种细菌细胞壁的糖肽中。β-丙氨酸是维生素泛酸和辅酶A的组分。 -Arg L-精氨酸：arginine。系统命名为(2S)-氨基-5-胍基戊酸。在生理条件下带正电荷，为编码氨基酸。是幼小哺乳动物的必需氨基酸。符号：R，Arg。 -Ile L-异亮氨酸：isoleucine。系统命名为(2S)-氨基-(3R)-甲基戊酸。是编码氨基酸。有两个手性碳原子，是哺乳动物的必需氨基酸。符号:I，Ile。 -Leu L-亮氨酸：leucine。系统命名为(2S)-氨基-4-甲基戊酸。是编码氨基酸。是哺乳动物的必需氨基酸。符号：L，Leu。 -CONH2 C端酰胺化
氨基酸个数:	36
分子式:	C₁₈₆H₃₁₃O₅₁N₅₇
平均分子量:	4163.83
精确分子量:	4161.36
等电点(PI):	12.52
pH=7.0时的净电荷数:	2.24
平均亲水性:	-0.42058823529412
疏水性值:	0.02
消光系数:	5500
标签:	人类免疫缺陷病(HIV)肽

Definition
Human immunodeficiency virus (HIV) is a lentivirus that causes acquired immunodeficiency syndrome (AIDS), a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections. Over 5000 HIV-related peptides have been synthesized, that inhibit different stages of viral life cycle.

Discovery
In 1983, two separate researchers Robert Gallo and Luc Montagnier independently declared that a novel retrovirus infecting AIDS patients. Several HIV related peptides including peptides (15-mers or 20-mers) of HIV glycoprotein 160 (gp160), gp120W16D, MN envelope (env) consensus B tat, consensus B VIF, HXB2 gag, SIVmac239, SIVmac239env, SIVmac239 gag have been used to study HIV life cycle. C34 peptide of Gp41 HIV Fragment is known as HR2, belongs to the helical region of gp41 of HIV, C-terminal heptad repeat 2 (HR2) defined as C helix or C peptide. It is known that HIV-1 enters cells by membrane fusion, C34 gp41 peptide is a potent inhibitors of HIV-1 fusion 1,2. The 86 amino acid trans-activator (Tat) protein of human immunodeficiency virus type 1 (HIV-1) is an RNA-binding transcriptional regulator. HIV-1 Tat proteins (wild type and Thr40Lys mutant) and the HIV-1 Tat peptide fragments Tat(32–48) and Tat(32–72) were chemically synthesized and used for HIV studies 3.

HIV (gp120) fragment (254-274), this fragment with sequence homology to a domain of the external envelope glycoprotein (gp120) of the human immunodeficiency virus (HIV) is important for HIV infectivity and antibody neutralization 4. HIV (gp120) fragment (421-438), derived from the CD4 attachment region of HIV gp120, inhibited the syncytial formation in vitro 5. HIV-1 gag protein p17 (76-84), HLA-A*0201-restricted immunodominant CD8 epitope of the HIV gag protein used for the characterization of CD8+ -T cells of HIV-positiv patients 6. HIV-1 rev protein (34-50), this arginine-rich fragment interacts specifically with RNA. It has been shown that rev protein and rev protein (34-50) bind IIB RNA with a similar dissociation constant of approx. 10 nM 7.

Structural Characteristics
The HIV type-1 belongs to the family Retroviridae and consists of two basic components: a core of ribonucleic acid (RNA), called the genome, and a protein component that surrounds the genome, called a capsid. The single-stranded RNA is tightly bound to nucleocapsid proteins and enzymes needed for the morphogenesis of the virion such as reverse transcriptase, proteases, ribonuclease and integrase. A matrix composed of the viral protein that surrounds the capsid. Viral envelope is composed of two layers of fatty molecules taken from the membrane of a human cell during budding process. There are 70 copies of a complex HIV protein that protrudes through the surface of the virus particle, known as Env, consists of a cap, glycoprotein (gp) 120, and a stem, gp41 molecules. This glycoprotein complex is important for fusion of virus to host cell. Both these surface proteins are important targets for treatments or HIV vaccines 8.

Mode of Action
HIV binds to a CD4 receptor and one of two co-receptors on the surface of a CD4+ T- lymphocyte. After fusion, the virus releases RNA, its genetic material, into the host cell. An HIV enzyme called reverse transcriptase converts the single- stranded HIV RNA to double-stranded HIV DNA. The newly formed HIV DNA enters the host cell's nucleus. The integrated HIV DNA is called provirus. The provirus may remain inactive for several years, producing few or no new copies of HIV. When the host cell receives a signal to become active, the provirus uses a host enzyme called RNA polymerase to create copies of the HIV genomic material, as well as shorter strands of RNA called messenger RNA (mRNA). The mRNA is used as a blueprint to make long chains of HIV proteins. An HIV enzyme called protease cuts the long chains of HIV proteins into smaller individual proteins. As the smaller HIV proteins come together with copies of HIV's RNA genetic material, a new virus particle is assembled. The newly assembled virus buds out from the host cell. During budding, the new virus acquires part of the cell's outer envelope. This envelope is embedded with viral glycoproteins which are necessary for host cell recognition.

Functions

CD8 cytotoxic, HIV-1 specific CD8 cytotoxic T lymphocyte (CTL) responses play a critical role in controlling HIV-1 replication. TCR avidity correlates with CTL function, and CTLs expressing TCRs with high avidity for their cognate MHC-viral peptide complex play an important in vivo role in neutralizing virus infections, terminating virus infection and delaying systemic AIDS virus dissemination from the mucosal inoculation site.

HIV-1 envelope transmembrane protein that contain highly positively charged amphipathic helices (designated LLP) in have both cytolytic and calmodulin (CaM) binding/inhibitory properties that contribute to cytopathogenesis during a viral infection.

HIV-1 vif, The human immunodeficiency virus type 1 (HIV-1) auxiliary gene vif is essential for virus propagation in peripheral blood lymphocytes, macrophages, and in some T-cell lines. (i) Vif protein binds HIV-1 PR (protease), but not covalently linked tethered PR-PR; (ii) the four amino acids residing at the N terminus of HIV-1 PR are essential for Vif/PR interaction; (iii) synthetic peptide derived from the N terminus of HIV-1 PR inhibits Vif/PR binding; and (iv) this peptide inhibits the propagation of HIV-1 in restrictive cells 9.

References

1. Bianchi E, Finotto M, Ingallinella P, Hrin R, Carella AV, Hou XS, Schleif WA, Miller MD, Geleziunas R, Pessi A (2005). Covalent stabilization of coiled coils of the HIV gp41 N region yields extremely potent and broad inhibitors of viral infection. PNAS., 102(36):12903-12908

2. de Rosny E, Vassell R, Jiang S, Kunert R, Weiss CD (2004). Binding of the 2F5 monoclonal antibody to native and fusion-intermediate forms of human immunodeficiency virus type 1 gp41: implications for fusion-inducing conformational changes. J. Virol., 78(5):2627-2631.
3. Klostermeier D, Bayer P, Kraft M, Frank RW, Rösch P (1997). Spectroscopic investigations of HIV-1 trans-activator and related peptides in aqueous solutions. Biophysical Chemistry, 63(2):87-96.

4. Ho DD, Kaplan JC, Rackauskas IE, Gurney ME (1988). Second conserved domain of gp120 is important for HIV infectivity and antibody neutralization. Science, 239(4843):1021-1023.

5. Morrow WJ, Williams WM, Whalley AS, Ryskamp T, Newman R, Kang CY, Chamat S, Köhler H, Kieber-Emmons T (1992). Synthetic peptides from a conserved region of gp120 induce broadly reactive anti-HIV responses. Immunology, 75(4):557-564.

6. Wilkinson J, Cope A, Gill J, Bourboulia D, Hayes P, Imami N, Kubo T, Marcelin A, Calvez V, Weiss R, Gazzard B, Boshoff C, Gotch F (2002). Identification of Kaposi's sarcoma-associated herpesvirus (KSHV)-specific cytotoxic T-lymphocyte epitopes and evaluation of reconstitution of KSHV-specific responses in human immunodeficiency virus type 1-Infected patients receiving highly active antiretroviral therapy. J. Virol., 76(6):2634-2640.

7. Kjems J, Calnan BJ, Frankel AD, Sharp PA (1992). Specific binding of a basic peptide from HIV-1 Rev. EMBO J., 11(3):1119-29.
8. Chan DC, Fass D, Berger JM, Kim PS (1997). Core structure of gp41 from the HIV envlope glycoprotein . Cell, 89:263–73.

9. Hutoran M, Britan E, Baraz L, Blumenzweig I, Steinitz M, Kotler M (2004). Abrogation of Vif function by peptide derived from the N-terminal region of the human immunodeficiency virus type 1 (HIV-1) protease. Virology, 330(1):261-270.
多肽Ac-Ser-Gly-Ile-Val-Gln-Gln-Gln-Asn-Asn-Leu-Leu-Arg-Ala-Ile-Glu-Ala-Gln-Gln-His-Leu-Leu-Gln-Leu-Thr-Val-Trp-Gly-Ile-Lys-Gln-Leu-Gln-Ala-Arg-Ile-Leu-NH2的合成步骤：

1、合成MBHA树脂：取若干克MBHA树脂（如初始取代度为0.5mmol/g）和1倍树脂摩尔量的Fmoc-Linker-OH加入到反应器中，加入DMF，搅拌使氨基酸完全溶解。再加入树脂2倍量的DIEPA，搅拌混合均匀。再加入树脂0.95倍量的HBTU，搅拌混合均匀。反应3-4小时后，用DMF洗涤3次。用2倍树脂体积的10%乙酸酐/DMF 进行封端30分钟。然后再用DMF洗涤3次，甲醇洗涤2次，DCM洗涤2次，再用甲醇洗涤2次。真空干燥12小时以上，得到干燥的树脂{Fmoc-Linker-MHBA Resin}，测定取代度。这里测得取代度为 0.3mmol/g。结构如下图：

2、脱Fmoc：取2.59g的上述树脂，用DCM或DMF溶胀20分钟。用DMF洗涤2遍。加3倍树脂体积的20%Pip/DMF溶液，鼓氮气30分钟，然后2倍树脂体积的DMF 洗涤5次。得到 H2N-Linker-MBHA Resin 。（此步骤脱除Fmoc基团，茚三酮检测为蓝色，Pip为哌啶）。结构图如下：

3、缩合：取2.33mmol Fmoc-Leu-OH 氨基酸，加入到上述树脂里，加适当DMF溶解氨基酸，再依次加入4.66mmol DIPEA，2.21mmol HBTU。反应30分钟后，取小样洗涤，茚三酮检测为无色。用2倍树脂体积的DMF 洗涤3次树脂。（洗涤树脂，去掉残留溶剂，为下一步反应做准备）。得到Fmoc-Leu-Linker-MBHA Resin。氨基酸：DIPEA：HBTU：树脂=3：6：2.85：1（摩尔比）。结构图如下：

4、依次循环步骤二、步骤三，依次得到

H2N-Leu-Linker-MBHA Resin

Fmoc-Ile-Leu-Linker-MBHA Resin

H2N-Ile-Leu-Linker-MBHA Resin

Fmoc-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Gly-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

H2N-Gly-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

Fmoc-Ser(tBu)-Gly-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin

以上中间结构，均可在专肽生物多肽计算器-多肽结构计算器中，一键画出。

最后再经过步骤二得到 H2N-Ser(tBu)-Gly-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHA Resin，结构如下：

5、乙酸酐反应连接：在上述树脂中，加入适当DMF后，再加入2.33mmol乙酸酐到树脂中，再加入4.66mmol DIPEA，鼓氮气反应30分钟。用2倍树脂体积的DMF 洗涤3次树脂（洗涤树脂，去掉残留溶剂，为下一步反应做准备）。得到Ac-Ser(tBu)-Gly-Ile-Val-Gln(Trt)-Gln(Trt)-Gln(Trt)-Asn(Trt)-Asn(Trt)-Leu-Leu-Arg(Pbf)-Ala-Ile-Glu(OtBu)-Ala-Gln(Trt)-Gln(Trt)-His(Trt)-Leu-Leu-Gln(Trt)-Leu-Thr(tBu)-Val-Trp(Boc)-Gly-Ile-Lys(Boc)-Gln(Trt)-Leu-Gln(Trt)-Ala-Arg(Pbf)-Ile-Leu-Linker-MBHAResin。结构如下：

6、切割：6倍树脂体积的切割液（或每1g树脂加8ml左右的切割液），摇床摇晃 2小时，过滤掉树脂，用冰无水乙醚沉淀滤液，并用冰无水乙醚洗涤沉淀物3次，最后将沉淀物放真空干燥釜中，常温干燥24小试，得到粗品Ac-Ser-Gly-Ile-Val-Gln-Gln-Gln-Asn-Asn-Leu-Leu-Arg-Ala-Ile-Glu-Ala-Gln-Gln-His-Leu-Leu-Gln-Leu-Thr-Val-Trp-Gly-Ile-Lys-Gln-Leu-Gln-Ala-Arg-Ile-Leu-NH2。结构图见产品结构图。

切割液选择：1）TFA：H2O=95%：5%

2）TFA：H2O：TIS=95%：2.5%：2.5%

3）三氟乙酸：茴香硫醚：1，2-乙二硫醇：苯酚：水=87.5%：5%：2.5%：2.5%：2.5%

（前两种适合没有容易氧化的氨基酸，例如Trp、Cys、Met。第三种适合几乎所有的序列。）

7、纯化冻干：使用液相色谱纯化，收集目标峰液体，进行冻干，获得蓬松的粉末状固体多肽。不过这时要取小样复测下纯度是否目标纯度。

8、最后总结：

杭州专肽生物技术有限公司（ALLPEPTIDE https://www.allpeptide.com）主营定制多肽合成业务，提供各类长肽，短肽，环肽，提供各类修饰肽，如：荧光标记修饰（CY3、CY5、CY5.5、CY7、FAM、FITC、Rhodamine B、TAMRA等），功能基团修饰肽（叠氮、炔基、DBCO、DOTA、NOTA等），同位素标记肽（N15、C13），订书肽（Stapled Peptide）,脂肪酸修饰肽（Pal、Myr、Ste），磷酸化修饰肽（P-Ser、P-Thr、P-Tyr），环肽（酰胺键环肽、一对或者多对二硫键环），生物素标记肽，PEG修饰肽，甲基化修饰肽等。

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